Category: 156267-13-9

Robison, Michael M.; Robinson, Bonnie L. published an article in 1955, the title of the article was 7-Azaindole. II. Conversion to 7-methyl-7H-pyrrolo-[2,3-b]pyridine and related compounds.Related Products of 156267-13-9 And the article contains the following content:

cf. C.A. 50, 1019g. 7-Azaindole (I) (5.90 g.) [prepared by a slight modification of the method described previously (loc. cit.)] in 75 cc. dry C6H6 refluxed 50 min. with 11.1 g. p-MeC6H4SO3Me, cooled, kept overnight, and filtered, the solid washed with EtOAc, and the white crystalline product (14.07 g.) dissolved in boiling CHCl3, diluted to turbidity with EtOAc, and cooled yielded 7-methyl-1H-pyrrolo[2,3-b]pyridinium p-toluenesulfonate (II), prisms, m. 134.0-4.5° (all m.ps. are corrected). I kept 3 days with 4 equivalents MeI, the excess MeI evaporated, and the residue washed with Et2O gave 100% impure 7-methyl-1H-pyrrolo[2,3-b]pyridinium iodide (III), m. 80-150°. Crude II (7.60 g.) in 15 cc. H2O saturated with cooling with K2CO3 and extracted with 600 cc. Et2O in 10 portions, the extract dried and evaporated, the brown oily residue in the min. amount hot 1:1 C6H6-hexane, treated with Darco, and evaporated on the steam bath, the residue chilled, and the yellow-brown solid residue dried in vacuo over KOH and distilled in a sublimation apparatus at 80-90° (bath) and 0.2 mm. yielded 2.31 g. crude 7-methyl-7H-pyrrolo[2,3-b]pyridine (IV), yellow solid, which dried in the m.p. tube in vacuo several months showed a m.p. of 48.5-50.5° (sealed tube); it liquefied rapidly in air; pKb 5.2. III gave similarly 88% 7H-pyrrolo[2,3-b]-pyridine, λ 245 (4.197), 309 (3.945), 385 mμ (log ε 2.991); pKb 5.1. The amine (0.31 g.), m. 44-6°, from the hydrolysis of II, and 20 cc. 20% aqueous NaOH refluxed 5.25 h., cooled, and extracted with Et2O, and the residue from the extract dried in vacuo over KOH yielded 0.28 g. IV, m. 44-6°. II (1.38 g.) in 15 cc. H2O treated with 1.14 g. picric acid and 0.41 g. anhydrous NaOAc yielded the picrate of IV, lemon-yellow needles, m. 209.5-10.5°. I (273 mg.) refluxed 6 h. with 20 cc. aqueous NaOH and extracted with Et2O gave 258 mg. unchanged I. IV (692.5 mg.) in 50 cc. 95% EtOH hydrogenated 25.5 h. at atm. pressure over 340 mg. Pt (reduced PtO2), the resulting yellow oil (506 mg.) in 10 cc. dry C6H6 kept 65 min. at room temperature with 429 mg. PhNCO, the C6H6 evaporated on the steam bath in a N stream, the residue warmed slightly with a few cc. H2O and 5 cc. 5% HCl, the solution filtered, the filtrate treated with Darco and basified strongly with excess K2CO3, the resulting oil chilled and scratched, and the solid washed and dried yielded 0.76 g. 1-phenyl-3-[2-(1-methyl-3-piperidyl)ethyl]urea (IVa), m. 100.5-2.0° (from cyclohexane) (sealed tube). 3-Pyridineacetonitrile (5.88 g.) in 80 cc. 95% EtOH and 20 cc. concentrated NH4OH hydrogenated 7 h. at 2 atm. pressure over 2-3 g. Raney Ni, filtered, the EtOH evaporated on the steam bath, the residual solution saturated with K2CO3 and extracted with CHCl3, and the extract distilled yielded 4.21 g. 3-(2-aminoethyl)pyridine (V), liquid, b15 114-19°. V treated with 2 equivalents picric acid in hot H2O gave the dipicrate, yellow needles, m. 213.5-14.0° (decomposition). V (1.22 g.) in 10 co. dry C6H6 treated 0.5 h. with 1.19 g. PhNCO and the product washed with C6H6 and dried in vacuo yielded 2.33 g. 1-phenyl-3-[2-(3-pyridyl)ethyl]urea (VI), needles, m. 114.5-15.5° (from 1:9 EtOH-H2O and from C6H6). VI (1.61 g.) and 9.5 g. MeI kept 26 h. under N, the excess MeI decanted, and the residue dried in vacuo yielded 3.07 g. 1-methyl-3-[2-(3-phenylureido)ethyl]pyridinium iodide (VII), hygroscopic, prisms, m. 71.5-4.5° (sealed tube) (from absolute EtOH). VII (1.485 g.) in 60 cc. 95% EtOH hydrogenated 8 h. at atm. pressure over 340 mg. prereduced PtO2, the resulting product dissolved in dilute HCl, filtered, and treated with excess K2CO3, and the oil rubbed gave 853 mg. IVa, m. 99.5-100.5° (sealed tube). Com. NaNH2 (1.95 g.) (finely powd.) in 100 cc. dry xylene treated dropwise with stirring with 5.90 g. I in 50 cc. dry xylene, the mixture refluxed 8 h., cooled to room temperature, treated with stirring during 0.5 h. with 7.1 g. MeI in 50 cc. xylene, refluxed 2 h., kept overnight at room temperature, and diluted with 75 cc. H2O and 20 cc. concentrated HCl, the xylene layer extracted with dilute acid, the combined aqueous extracts washed with Et2O, basified with solid K2CO3, and extracted with 600 cc. Et2O in 6 portions, the extract dried and evaporated, and the residue distilled, the resulting 4 g. mixture washed with cyclohexane, steam distilled, treated with K2CO3, extracted with Et2O, and distilled gave 1.28 g. 1-methyl-7-azaindole (VII), hygroscopic oil, b21 112-16°, nD26 1.5959, d22 1.107; it developed a yellow color on standing. 2-Amino-3-picoline (21.6 g.) in 100 cc. dry Et2O refluxed 2 h. with 7.8 g. NaNH2, cooled to room temperature, treated with 28.4 g. MeI in 50 cc. dry Et2O with stirring during 35 min., refluxed 1 h., cooled, diluted with 40 cc. H2O, and treated with excess K2CO3, the aqueous layer extracted with Et2O, and the extract dried and distilled gave 20.75 g. crude alkylation product, yellow oil, b22 105-15°; 65.94 g. crude product in 200 cc. dry pyridine treated with cooling and swirling during 12 min. with 170.2 g. BzCl, heated 0.5 h., cooled, poured below 10° into 250 cc. concentrated HCl and 790 cc. H2O, and filtered, the filtrate basified and extracted with Et2O, and the extract distilled gave 85.36 g. N-methyl-N-(3-methyl-2-pyridyl)benzamide (VIII), b22 210° to b20 220° needles, m. 92.0-3.5° (from 1:1 EtOH-H2O and from hexane). VIII (85.36 g.) refluxed 1 h. with 202 cc. concentrated HCl, cooled, filtered, basified strongly with K2CO3, and extracted with Et2O, and the extract dried and distilled gave 82.6% pure 2-methylamino-3-picoline (IX), hygroscopic oil, b21 113°, m. about 21°. IX (32.96 g.) formylated by the method of Clemo and Swan (C.A. 40, 581.1), the volatile materials distilled off after 2 days up to 60° (23 mm.), the residue dissolved in 65 cc. H2O, treated with excess K2CO3, and extracted with Et2O, and the extract dried and distilled gave 26.38 g. N-methyl-N-(3-methyl-2-pyridyl)formamide (X), oil, b19 151-56°. X added to PhNHNa and HCO2K, the reaction carried out in the usual manner (loc. cit.), the mixture treated with H2O and AcOH, and steam distilled, the distillate treated with excess HCl, decolorized with Darco, treated with excess Ac2O and NaOAc, and filtered, the filter residue washed with H2O and dilute HCl, and the combined filtrates basified with K2CO3 did not give any liquid product. X treated with 1.5 mol KOEt by the method of Tyson (C.A. 35, 5889.9) 0.5 h. at 350°, the dark mixture cooled, decomposed with H2O, and steam distilled, the distillate acidified with HCl, washed with Et2O, basified with K2CO3, and extracted with Et2O, the extract dried and distilled, and the distillate, b18 108-12°, nD30 1.5665, treated with BzCl, poured into aqueous K2CO3, allowed to stand 40 min., and extracted with Et2O gave the benzoate of IX, b19 212°, m. 91.5-96°. IV (0.52 g.) kept 28 h. with 5 cc. MeI under N, the excess MeI evaporated, and the solid residue dried gave 1.37 g. impure 1,7-dimethyl-1H-pyrrolo[2,3-b]pyridinium iodide (XI), white needles, m. 249.5° (decomposition), λ 227 (4.522), 296 μ (log ε 3.888). VII (652 mg.) treated 60 h. under N with 5 cc. MeI, the excess MeI evaporated in a N stream, and the residue washed with cyclohexane gave 597 mg. XI; m. 250.5° (decomposition) (from absolute EtOH); the cyclohexane washings evaporated gave 275 mg. VII. The UV absorption spectra of I, IV, VII, and 7-azaskatole are recorded. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

N,3-Dimethylpyridin-2-amine(cas:156267-13-9) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On August 6, 1996, Suzuki, Masashi published a patent.Formula: C7H10N2 The title of the patent was Preparation of methylaminopyridine derivatives in high-yield. And the patent contained the following:

The title compounds (I; R = C1-4 alkyl, n = 1-2, X = NHMe) can be efficiently and economically produced by reaction of I (X = NH2, R, n = same as above) with a mixture of (HCO)2O and (AcO)2O or with HCO2H in the presence of (AcO)2O, followed by reduction of formyl group. I are useful intermediates in the production of drugs and pesticides. Thus, I (Rn = 4-Me and 6-Me, X = NH2) was reacted with HCO2H in the presence of (AcO)2O to give 85% I (Rn = 4-Me and 6-Me, X = NHCHO), which was reduced by LiAlH4 to give 97% I (Rn = 4-Me and 6-Me, X = NHMe). The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Formula: C7H10N2

The Article related to methylaminopyridine preparation, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Formula: C7H10N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On October 16, 2008, Ashweek, Neil; Chen, Mi; Coon, Timothy Richard; Ewing, Todd; Jiang, Wanlong; Moree, Willy; Rowbottom, Martin; Wade, Warren; Zhao, Liren; Zhu, Yun-Fei; Yu, Jinghua; Beaton, Graham published a patent.Related Products of 156267-13-9 The title of the patent was Preparation of benzenesulfonylamide derivatives as Gonadotropin-releasing hormone receptor antagonists. And the patent contained the following:

Title compounds represented by the formula I [wherein A = pyridyl, Ph, quinolinyl, etc.; R1a = H, halo, alkyl, etc.; R1b, R1c = independently H, halo, OH, etc.; R1d = F, Cl, Me, CF3 or cyano; R2 = alkyl-(R5)p; R2a = (un)substituted Ph, aryl, alkyl, etc.; or R2R2a = (un)substituted heterocycle; R5 = independently H, OH, amino, etc.; p = 1-3; and stereoisomers, esters, solvates, and pharmaceutically acceptable salts thereof] were prepared as Gonadotropin-releasing hormone receptor (GnRH) antagonists. For example, II was provided in a multi-step synthesis starting from 1-bromo-2-chloro-4-fluorobenzene. I were tested in one or more of the peptide competitive human receptor binding assays and showed Ki values of 1 μM or less. Thus, I and their pharmaceutical compositions are useful for the treatment of a variety of sex-hormone related conditions in both men and women. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

The Article related to benzenesulfonylamide pyridinyl preparation gonadotropin releasing hormone receptor antagonist, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On October 16, 2008, Beaton, Graham; Chen, Mi; Coon, Timothy Richard; Ewing, Todd; Jiang, Wanlong; Lowe, Richard; Moree, Willy; Smith, Nicole; Wade, Warren; Zhao, Liren; Zhu, Yun-Fei; Rowbottom, Martin; Ashweek, Neil published a patent.Synthetic Route of 156267-13-9 The title of the patent was Preparation of benzenecarboxamide derivatives as Gonadotropin-releasing hormone receptor antagonists. And the patent contained the following:

Title compounds represented by the formula I [wherein A = pyridyl, Ph, quinolinyl, etc.; R1a = H, halo, alkyl, etc.; R1b, R1c = independently H, halo, OH, etc.; R1d = F, Cl, Me, CF3 or cyano; R2 = alkyl-(R5)p; R2a = (un)substituted Ph, (hetero)aryl or alkyl; R5 = independently H, OH, amino, etc.; p = 1-3; and stereoisomers, esters, solvates, and pharmaceutically acceptable salts thereof] were prepared as Gonadotropin-releasing hormone receptor (GnRH) antagonists. For example, II was provided in a multi-step synthesis starting from 3-bromo-4-chlorobenzoic acid. I were tested in one or more of the peptide competitive human receptor binding assays and showed Ki values of 1 μM or less. Thus, I and their pharmaceutical compositions are useful for the treatment of a variety of sex-hormone related conditions in both men and women. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Synthetic Route of 156267-13-9

The Article related to benzenecarboxamide pyridinyl preparation gonadotropin releasing hormone receptor antagonist, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Synthetic Route of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tanaka, Katsumasa; Hattori, Hiroshi; Yabe, Ryota; Nishimura, Takahiro published an article in 2022, the title of the article was Ir-Catalyzed cyclization of α,ω-dienes with an N-methyl group via two C-H activation steps.Related Products of 156267-13-9 And the article contains the following content:

Iridium-catalyzed sp3 C-H alkylation of an N-Me group with 1,5- and 1,6-dienes proceeded to give five- and six-membered carbocyclic compounds, resp., in high yields. The reaction involved intermol. alkylation of the N-Me group with a vinyl moiety and subsequent intramol. cyclization at the β-position of the initially formed alkylated intermediate. The reaction using a chiral bidentate phosphine ligand enabled the asym. synthesis of the cyclic compounds The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

The Article related to methylpyridinamine diene iridium catalyst regioselective bond activation alkylation cyclization, cycloalkylmethylpyridinamine enantioselective preparation, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On March 3, 1994, Rewcastle, Gordon W.; Denny, William A. published an article.Quality Control of N,3-Dimethylpyridin-2-amine The title of the article was Lithiation routes to oxindoles and 2-indolinethiones: precursors to 2,2′-dithiobisindoles with tyrosine kinase inhibitory properties. And the article contained the following:

N-Substituted oxindoles, e.g. I, and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 resp. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with di-Me disulfide. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Quality Control of N,3-Dimethylpyridin-2-amine

The Article related to dithiobisindole preparation tyrosine kinase inhibitory, oxindole substituted, indolinethione substituted, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Quality Control of N,3-Dimethylpyridin-2-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On November 7, 1995, Dobrusin, Ellen M.; Showalter, Howard D. H.; Denny, William A.; Palmer, Brian D.; Rewcastle, Gordon W.; Tercel, Moana; Thompson, Andrew M. published a patent.Related Products of 156267-13-9 The title of the patent was Preparation of 2-indolyldisulfides and analogs as protein tyrosine kinase inhibitors and antitumor agents. And the patent contained the following:

Title compounds [I; R1 = H, halo, alkyl, alkoxy, etc.; R2 = (acyl)alkyl, acyl, CH:CHCO2H, etc.; R3 = H, alkyl, CH2Ph; R4 = SH, SnR, SeH, SenR, etc.; R = H, alkyl, (hetero)aryl, I in which R4 = bond, etc.; R4R5 = S, Se; R5R6 = bond; R6 = H; n = 1-3] were prepared 2Hus, 1-methyl-2-indolinone was treated with P2S5 and the product condensed with PhNCO to give, after oxidation, title compound II which had IC50 of 3-4μM against growth factor mediated mitogenesis in vitro. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

The Article related to indolyldisulfide preparation protein tyrosine kinase inhibitor, antitumor indolyldisulfide preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On May 22, 2014, Chatterjee, Arnab Kumar; Nagle, Advait Suresh; Paraselli, Prasuna; Leong, Seh Yong; Roland, Jason Thomas; Mishra, Pranab Kumar; Yeung, Bryan K. S.; Zou, Bin published a patent.Formula: C7H10N2 The title of the patent was Preparation of imidazopyrazines for treating parasitic diseases. And the patent contained the following:

The invention is related to the preparation of title compounds I [n = 0-2; p = 0-3; A = aryl, heteroaryl, and fused bycyclyl comprising a heterocycloalkyl fused to a phenyl; B = the imidazo[1,2-a]pyrazine fused ring depicted in I; D = Ph, heteroaryl, cycloalkyl, heterocycloalkyl, fused bicyclyl comprising a heterocycloalkyl fused to a phenyl; L = *CO, alkylene, *NR2CO, *CH2NR2, etc.; * represents the point of attachment of L to ring B; R2 = H, alkyl, R0-alkylene ; R0 = alkoxyamino, heteroaryl, alkylamino, etc.; R1 = independently at each occurrence halo, CN, NH2 and derivatives; R15, R16 = independently H, alkyl, haloalkyl; R17 = independently at each occurrence halo, OH and derivatives, SO2NH2 and derivatives, etc.], or a pharmaceutical acceptable salt, tautomer or stereoisomer, useful for treating, preventing, inhibiting, ameliorating, or eradicating the pathol. and/or symptomol. of a disease, such as malaria, caused by a Plasmodium parasite. Thus, a multi-step synthesis starting from chloroacetaldehyde and 5-amino-2-pyrazinecarboxylic acid Et ester was given for II. I were tested for their capacity to inhibit proliferation of parasitemia in 3D7 Plasmodium falciparum infected red blood cells and had EC50 of 10 μM or less. I showed delay of the proliferation of P. yoelii in liver cells in a P. yoelii sporozoite invasion assay (EC50 for II = 14 nM). The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Formula: C7H10N2

The Article related to imidazopyrazine preparation antimalarial plasmodium falciparum, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C7H10N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On June 24, 1994, Rewcastle, Gordon W.; Palmer, Brian D.; Dobrusin, Ellen M.; Fry, David W.; Kraker, Alan J.; Denny, William A. published an article.COA of Formula: C7H10N2 The title of the article was Tyrosine Kinase Inhibitors. 3. Structure-Activity Relationships for Inhibition of Protein Tyrosine Kinases by Nuclear-Substituted Derivatives of 2,2′-Dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamide). And the article contained the following:

A series of indole-substituted 2,2′-dithiobis(1-methyl-N-phenyl-1H-indole-3-carboxamides) I (R = H, 5-Cl, 6-Me, 7-OH, 5-MeO, etc.) were prepared and evaluated for their ability to inhibit the tyrosine kinase activity of both the epidermal growth factor receptor (EGFR) and the nonreceptor pp60v-src tyrosine kinase. The compounds were synthesized by conversion of appropriate 1-methyloxindoles to 1-methyl-2-indolinethiones with P2S5 followed by subsequent reaction with NaH and Ph isocyanate and oxidative dimerization of the resulting 2,3-dihydro-N-phenyl-2-thioxo-1H-indole-3-carboxamides. The parent compound and many of the substituted analogs were moderately potent inhibitors of both kinase enzymes, but no clear relationships were seen between substitution on the indole ring and inhibitory activity. While 4-substituted compounds were generally inactive, 5-substituted derivatives with electron-withdrawing groups showed inhibitory activity. However, none of the substituted compounds showed significantly better activity than the unsubstituted parent compound There was generally a good correlation between activity against the EGFR and pp60v-src kinases, but several compounds did show some specificity (>20-fold) of inhibition; 5-Cl and 5-Br derivatives preferentially inhibited pp60v-src, while the 5-CF3 compound preferentially inhibited EGFR. Selected compounds from the series were found to inhibit the growth of Swiss 3T3 fibroblasts with IC50s in the range 2-25 μM, the most active being 4-substituted derivatives The compounds inhibited bFGF-mediated protein tyrosine phosphorylation in intact cells more effectively than EGFR- or PDGF-mediated phosphorylation. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).COA of Formula: C7H10N2

The Article related to dithiobismethylphenylindolecarboxamide protein tyrosine kinases inhibitor, indolecarboxamide dithiobismethylphenyl protein tyrosine kinases inhibitor, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.COA of Formula: C7H10N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On March 3, 1994, Rewcastle, Gordon W.; Denny, William A. published an article.Quality Control of N,3-Dimethylpyridin-2-amine The title of the article was Lithiation routes to oxindoles and 2-indolinethiones: precursors to 2,2′-dithiobisindoles with tyrosine kinase inhibitory properties. And the article contained the following:

N-Substituted oxindoles, e.g. I, and 2-indolinethiones can be prepared by lithiation of carboxyl protected N,2-dimethylanilines followed by quenching with CO2 or CS2 resp. 2-Indolinethione derivatives are also available via demethylation of 2-methylthioindoles, which are prepared by lithiation of N-substituted indoles and treatment with di-Me disulfide. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Quality Control of N,3-Dimethylpyridin-2-amine

The Article related to dithiobisindole preparation tyrosine kinase inhibitory, oxindole substituted, indolinethione substituted, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Quality Control of N,3-Dimethylpyridin-2-amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem