Day: April 19, 2022

Reference of 887266-57-1, Adding some certain compound to certain chemical reactions, such as: 887266-57-1, name is 3-Fluoro-2-hydrazinylpyridine,molecular formula is C5H6FN3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 887266-57-1.

Under argon, a solution of methyl 2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2- hydroxypropyl] -4,5-dihydro- lH-l,2,4-triazol-1-yl}ethanimidate (Example 2A, 150 mg, 396 muiotaetaomicron) in THF (1.5 ml) was treated at 0C with N,N-diisopropylethylamine (210 mu, 1.2 mmol) and (2S)-1- chloro-1-oxopropan-2-yl acetate (55 mu, 440 muiotaetaomicron) and stirred at 0C for 30 min. 3-Fluoro-2- hydrazinylpyridine (55.4 mg, 436 muiotaetaomicron) was then added and the resulting mixture was stirred overnight at room temperature and evaporated. The residue was purified by preparative HPLC (Method 4) affording 152 mg (67% of th.) of the title compound.LC-MS (Method 1): Rt = 1.01 min; MS (ESIpos): m/z = 570 [M+H]+ -NMR (400 MHz, DMSO-d6) delta [ppm]: 8.46 (br. d, 1H), 8.23-8.05 (m, 1H), 7.88-7.53 (m, 5H), 6.89 (d, 1H), 5.93 (q, 1H), 5.12 (m, 2H), 4.30 (m, 1H), 4.08-3.71 (m, 2H), 1.79 (s, 3H), 1.59 (d, 3H).

According to the analysis of related databases, 887266-57-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; COLLIN-KROePELIN, Marie-Pierre; KOLKHOF, Peter; NEUBAUER, Thomas; FUeRSTNER, Chantal; POOK, Elisabeth; TINEL, Hanna; SCHMECK, Carsten; WASNAIRE, Pierre; SCHIRMER, Heiko; LUSTIG, Klemens; GRIEBENOW, Nils; (195 pag.)WO2019/81302; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52311-50-9, 2-Chloro-4-ethoxypyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, SDS of cas: 52311-50-9, blongs to pyridine-derivatives compound. SDS of cas: 52311-50-9

To a degassed mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide ( 9.4g, 38 mmol) and 2-chloro-4-ethoxypyridine ( 5g, 31.7 mmol) in dioxane was added Brettphos-prePd (catalytic amount) and CS2CO3 (12.3 g, 37.8 mmol) under N2 atmosphere. The mixture was heated to 100 C and stirred for 3.5 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated, and the residue was purified on silic-gel (PE: EA = 100% ~ 30%) to give N-(4- ethoxypyridin-2-yl)-4-(4,4, 5, 5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)benzamide (8.8 g, yield 75%). 1HNMR (400MHz, CDC13): 5=8.74 (s, 1 H), 8.05-8.02(m, 1 H), 8.01 (s, 1 H), 7.94-7.89 (m, 4 H), 6.60-6.59 (m, 1 H), 4.20-4.14 (m, 2 H), 1.47-1.43 (m, 3 H), 1.36 (s, 12 H), MS (ESI): M/Z (M+l)=369.19.

The synthetic route of 52311-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WU, Hao; KIM, Ronald M.; LIU, Jian; GAO, Xiaolei; BOGA, Sobhana Babu; GUIADEEN, Deodialsingh; LIU, Shilan; YANG, Chundao; WANG, Hongjian; WO2014/113932; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 1122-43-6, blongs to pyridine-derivatives compound. Safety of 2,6-Dimethyl-3-hydroxypyridine

To a solution of 2,6-dimethyl-3-pyridinol (3 g, 24.35 mmol) in THF (30 ml) at r.t., were added Cs2CO3 (15.87 g, 48.71 mmol) and 3,4-difluoro-l-nitro-benzene (3.87 g, 24.35 mmol). The reaction mixture was heated at reflux for 2 h. After cooling to r.t. the solids were filtered off and the filtrate was evaporated to dryness. The crude product was purified by column chromatography (silica gel; DCM/7M solution of NH3 in MeOH up to 2% as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D21 (5.88 g, 92 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-43-6, its application will become more common.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; DE LUCAS OLIVARES, Ana, Isabel; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/130423; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1196157-14-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1196157-14-8, name is 4-Bromo-5-methylpicolinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of a 60% dispersion of NaH in mineral oil (0.29 g, 7.25 mmol) in DME (2 niL) at – 30 C was added a solution of ethyl 2-phosphonoacetate (1.46 mL, 7.29 mmol) in DME (13 mL), and the mixture was stirred at this temperature for 30 min. To this solution was added a solution of 4-bromo-5-methylpyridine-2-carbaldehyde (64) (1.32 g, 6.60 mmol) in DME (3 mL), and the reaction was stirred at -30 C for 1.5 h and then poured into water (50 mL) and extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated NH4CI solution and then brine, dried over sodium sulfate, filtered and concentrated in vacuo to give a crude product that was purified by column chromatography (150 mL Si02, ethyl acetate:hexanes 1 :9) to give 65 (1.553 g, 87%) as a colorless crystalline solid: ? NMR (400 MHz, CDCI3) ? 8.41 (s, 1H), 7.59 (d, J= 15.6, 1H), 7.58 (s, 1H), 6.88 (d, J= 15.6, 1H), 4.25 (q, J= 7.2, 2H), 2.38 (s, 3H), 1.31 (t, J= 7.2, 3H); 13C NMR (100.6 MHz, CDC13) ? 166.4, 151.6, 150.8, 141.6, 135.4, 134.7, 127.3, 122.9, 60.6, 19.4, 14.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1196157-14-8, 4-Bromo-5-methylpicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; ARIZONA BOARD OF REGENTS, A BODY CORPORATE OF THE STATE OF ARIZONA ACTING FOR AND ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl, E.; JURUTKA, Peter, W.; MARSHALL, Pamela, A.; WO2013/40227; (2013); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 135900-33-3, Adding some certain compound to certain chemical reactions, such as: 135900-33-3, name is 6-(Trifluoromethoxy)pyridin-3-amine,molecular formula is C6H5F3N2O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 135900-33-3.

[0293] Compound Int-5 (Example 122) (90 mg, 0.43 mmol, 1.0 eq) and 6- (trifluoromethoxy)pyridin-3-amine (84 mg, 0.47 mmol, 1.1 eq) were dissolved in DMF (3 mL), and the resulting mixture was cooled down to 0 C. Then HATU (181 mg, 0.47 mmol, 1.1 eq) and DIPEA (0.16 mL, 0.868 mmol, 2.0 eq) were added to the reaction mixture at 0 C. The reaction mixture was allowed to warm up to room temperature, and stirred at room temperature for 3 hrs. The progress of the reaction was monitored by LCMS and TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water. The formed solid was filtered, washed and dried in vacuo to give 40 mg of the desired compound 128 as an off-white solid in 25% yield. 1H NMR (400 MHz, DMSO-de): delta 11.12 (s, 1H), 9.03-9.02 (dd, J = 4.4 Hz, 2.0 Hz, 1H), 8.68-8.69 (d, J = 2.4 Hz, 1H), 8.46-8.44 (d, J = 7.6 Hz, 1H), 8.39-8.36 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 8.30-8.31 (m, 2H), 7.70- 7.67 (dd, J = 8.4 Hz, 4.0 Hz, 1H), 7.39-7.37 (d, J = 8.8 Hz, 1H). 99.45% purity by LCMS; m/z =368.11 [M+H]+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 135900-33-3, 6-(Trifluoromethoxy)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTAVALON, INC.; DNEPROVSKAIA, Elena, V.; HOLZWARTH, Michael, S.; RYCHNOVSKY, Scott, D.; (184 pag.)WO2018/85348; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 178876-83-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 178876-83-0, name is Methyl 6-amino-3-bromopicolinate. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of methyl 6-amino-3-bromopicolinate (2.00 g, 8.66 mmol, 1 eq) in EtOH (15 mL) was added chloroacetaldehyde (13.6 g, 86.58 mmol, 50% purity, 10 eq) and NaHC03 (1.24 g, 14.72 mmol, 1.7 eq). The mixture was stirred at 95 C for 5.5 hours (hr). The reaction mixture was filtered and concentrated under reduced pressure. The residue was adjusted to pH=9 with K2C03 aqueous solution and extracted with chloroform. The combined organic layers were washed with brine, and dried over MgS04. The concentrated residue was purified by flash chromatography (Si02, pentane/ethyl acetate/MeOH = 2: 1 :0.03). Example 1 A (2.0 g, 91% yield) was obtained as a brown solid. Mass spectrum (ESI), m/z 255.0 and 257.1 [M + H]+.

According to the analysis of related databases, 178876-83-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHRYSALIS, INC.; GWALTNEY, Stephen; (147 pag.)WO2017/214413; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1026796-81-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, molecular weight is 215.05, as common compound, the synthetic route is as follows.

To a 15 mL vial was added N-(4-bromopyridin-2-yl)acetamide (205.8 mg, 0.957 mmol), (3-fluoro-4-hydroxyphenyl)boronic acid (239 mg, 1.531 mmol), and Na2C03 (1.435 mL, 2.87 mmol) in dioxane (3 mL) under nitrogen to give a colorless solution. l, -bis(diphenylphosphino)ferrocenepalladium(II) di chloride, toluene (39.4 mg, 0.048 mmol) was added under nitrogen. The vial was sealed and heated at 130 C (microwave) for 2 h. The mixture was partitioned between water and EtOAc. The layers were separated. The organic layer was washed with brine, dried Na2S04) and concentrated under reduced pressure to obtain N-(4-(3-fluoro-4- hydroxyphenyl)pyridin-2-yl)acetamide (200 mg, 0.812 mmol, 85% yield) as a tan solid. LCMS (ESI) m/e 247.0 [(M+H)+, calcd C13H12F1N2O2, 247.1]; LC/MS retention time (method A): /R = 1.51 min.

Statistics shows that 1026796-81-5 is playing an increasingly important role. we look forward to future research findings about N-(4-Bromopyridin-2-yl)acetamide.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BRONSON, Joanne J.; CHEN, Ling; DITTA, Jonathan L.; DZIERBA, Carolyn Diane; JALAGAM, Prasada Rao; LUO, Guanglin; MACOR, John E.; MAISHAL, Tarun Kumar; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; SISTLA, Ramesh Kumar; THANGAVEL, Soodamani; (485 pag.)WO2017/59085; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 60289-67-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.60289-67-0, name is 1-(Pyridin-3-yl)propan-1-amine, molecular formula is C8H12N2, molecular weight is 136.19, as common compound, the synthetic route is as follows.

General procedure: To a solution of ethyl 2- chlorothieno[3,2-(/Jpyrimidine-4-carboxylate (100 mg, 0.41 mmol) and DIEA (0.22 mL, 1.23 mmol) in NMP (3 mL) was added (6-methoxypyridin-3-yl)methanamine hydrochloride (commercially obtained from PharmaBlock, Sunnyvale, CA) (97 mg, 0.89 mmol). The reaction mixture was stirred at 130 C for 3 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with 25% aqueous NaCl solution, then with brine three times and dried. The solvent was evaporated and the residue was purified by flash chromatography (24g, HP silica, Teledyne Isco) eluting with 2% to 100% solvent A (DCM/MeOH/NH4OH, 100/10/1) in DCM to provide 2-chloro-N-((6-methoxypyridin-3- yl)methyl)thieno[3,2-Patent; CORVUS PHARMACEUTICALS, INC.; LI, Zhihong; FILONOVA, Lubov, Konstantinovna; BRADLEY, Erin, Kathleen; VERNER, Erik; (816 pag.)WO2019/46784; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 19235-89-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 19235-89-3, name is 4-Chloropyridine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

2-Acetyl-4-chloropyridine: To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0 C. was added dropwise over 20 min a 2M solution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 h. The mixture was cooled to 0 C. and 2M aqueous HCl (100 ml) added. The mixture was made basic with saturated aqueous sodium bicarbonate (~80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluding with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4-chloropyridine. 1H-NMR (DMSO-d6) delta: 8.59 (1H, d, J=5.1 Hz), 8.04 (1H, d, J=1.8 Hz), 7.47 (1H, dd, J=1.8, 5.1 Hz), 2.72 (3H, s).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 19235-89-3, 4-Chloropyridine-2-carbonitrile.

Reference:
Patent; Nakao, Kazunari; Stevens, Rodney William; Kawamura, Kiyoshi; Uchida, Chikara; Koike, Hiroki; Caron, Stephane; US6608070; (2003); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 165547-79-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.165547-79-5, name is 4-Chloro-3-nitro-2(1H)-pyridinone, molecular formula is C5H3ClN2O3, molecular weight is 174.54, as common compound, the synthetic route is as follows.

To a suspension of 4-chloro-3-nitro-2-pyridone (1.0 g, 5.7 mmol) and K2CO3 (1.6 g, 11.5 mmol) in DMA (5 mL) was added Mel (0.72 mL, 11.5 mmol). The rxn mixture was heated to 45C and stirred for 1h. It was quenched with H2O, acidified to pH 5 with a 25% aq. soln. of HCI and extracted with EtOAc (3x). The combined org. phases were washed with brine, dried over MgSCh and concentrated in vacuo. LC-MS: tR=0.60 min ; [M+H]+: 189.15 (0934) 1H NMR (400 MHz, DMSO-d6)5: 8.10 (d, J = 7.4 Hz, 1 H), 6.70 (d, J = 7.4 Hz, 1 H), 3.55 (s, 3 H)

Statistics shows that 165547-79-5 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-nitro-2(1H)-pyridinone.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem