Day: April 15, 2022

Synthetic Route of 1220910-89-3 , The common heterocyclic compound, 1220910-89-3, name is Benzyl (3-fluoro-4-(6-(2-methyl-2H-tetrazol-5-yl)pyridin-3-yl)phenyl)carbamate, molecular formula is C21H17FN6O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To the kettle was added tetrahydrofuran (20 L)And benzyl N- [3-fluoro-4- [6- (2-methyl- 2H- tetrazolium- 5 -yl) -3-pyridyl] phenyl] carbamateCompound (II) (1 Kg, 2.47 mol),0 ~ 30 C After mixing,1,3-Dimethyl-3,4,5,6-tetrahydro-2-pyrimidone was added sequentially (DMPU, 0.63 Kg, 4.94 mol, 2 equivalents),Lithium tert-butoxide (0.396 Kg, 4.94 mol, 2 equivalents)Add R-glycidyl butyrate(0.39 Kg, 2.72 mol, 1.1 equivalents)0 ~ 30 C for 15 hours.After the reaction,The reaction was quenched by adding a mass-volume ammonium chloride solution (1 Kg / 10 L)Concentrated under reduced pressure,The residue was added to methanol (10 L)Stirred for 0.5 hours to give suction filtration,The filter cake was washed with methanol,45 ~ 50 C under vacuum to give a white solid(5R) -3- (4- (6- (2-methyl- 2H- tetrazolium- 5-yl) -3-pyridyl) -3- fluorophenyl) -5-hydroxymethyl oxazoline -2-one Compound (III) (0.87 Kg, yield: 95%).

The synthetic route of 1220910-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing You Ke Pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Co., Ltd.; Nanjing You Ke Bio-pharmaceutical Group Co., Ltd.; Li Shang; Che Xiaoming; Zhao Zanzan; Zhu Suhua; Xue Yuquan; Zhang Feng; (7 pag.)CN106317114; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 933721-91-6, Imidazo[1,2-a]pyridin-8-ylmethanamine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

A solution of compound 5e (60 mg, 0.15 mmol) and compound 19c (26 mg, 0.18 mmol) in ethanol (0.5 mL) was irradiated at 180 C. in a microwave instrument for two 30 min intervals, then concentrated. The residue was dissolved in methyl sulfoxide and purified by reversed-phase chromatography to furnish the title compound 188 as its trifluoroacetate salt. 1H NMR (methanol-d4): delta 8.66 (d, 1H, J=6.8 Hz), 8.20 (d, 1H, J=2.2 Hz), 8.01 (d, 1H, J=2.2 Hz), 7.46 (d, 1H, J=7.4 Hz), 7.33 (d, 2H, J=8.6 Hz), 7.28 (t, 1H, J=7.0 Hz), 7.15 (d, 2H, J=8.6 Hz), 6.88 (d, 2H, J=8.8 Hz), 6.83 (d, 2H, J=8.8 Hz), 5.15 (s, 2H), 4.96 (s, 2H), 4.88 (s, 2H), 3.78 (s, 3H), 3.75 (s, 3H); HRMS m/z (M+H)+ calcd for C27H27N6O4 499.2094, found 499.2052.

The synthetic route of 933721-91-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Flores, Christopher M.; Wade, Paul R.; US2011/319400; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 185017-72-5, name is 3-Bromo-2-chloro-6-picoline. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5BrClN

[0415] To a stirred solution of sodium metal (4.46 g, 194 mmol) in MeOH (200 mL) under an argon atmosphere was added 3-bromo-2-chloro-6-methylpyridine (20 g, 97 mmol) at 0 C. The reaction mixture was stirred at 100 C for 4 h in a sealed tube. After consumption of starting material (by TLC), volatiles were evaporated in vacuo. The residue was quenched with water (200 mL) and extracted with EtOAc (2 x 250 mL). The combined organic extract was dried over sodium sulfate, filtered and concentrated in vacuo to obtain 3-bromo-2- methoxy-6-methylpyridine (18 g, 92%) as colorless liquid.?H-NMR (CDC13, 400 MHz): 7.61 (d, 1H), 6.60 (d, 1H), 3.99 (s, 3H), 2.39 (s, 3H); LCMS:99.6%; 201.8 (M+1); (column; Ascentis Express C-18 (50 x 3.0 mm, 2.7 jtm); RT 2.67 mm; mobile phase: 0.025% Aq TFA+5% ACN: ACN+5% 0.025% Aq TFA; T/B%: 0.01/5, 0.5/5, 3/100, 5/100; flow rate: 1.2 mL/min) (Gradient); TLC: 10% EtOAc/ Hexane (R1 0.7). Synthesis of 5-bromo-6-methoxypicolinic acid:

With the rapid development of chemical substances, we look forward to future research findings about 185017-72-5.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.)WO2017/31325; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 185017-72-5, name is 3-Bromo-2-chloro-6-picoline, the common compound, a new synthetic route is introduced below. SDS of cas: 185017-72-5

a) 1-(2-Chloro-6-methylpyridin-3-yl)cyclobutanol A suspension of molecular sieves (4 A) and 3-bromo-2-chloro-6-methylpyridine (CAN 185017-72-5, 5 g, 24.2 mmol) in THF (50 mL) was cooled to -15 C. 1.3 M isopropyl magnesium chloride lithium chloride complex solution in THF (19.6 mL, 25.4 mmol) was added within 30 mm. Stuffing was continued for 1 h at -15 C. Cyclobutanone (1.87 g, 2.00 mL, 26.6 mmol) was slowly added. Stirring was continued for 2 h at -15 C and for further 2 h at 0 C. Water (2.5 mL) was added, the mixture was concentrated in vacuo, and poured onto sat. aqueous NH4C1 solution. The mixture was extracted with EtOAc (2 x 100 mL).The combined extracts were washed with ice water (50 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 140 g, heptane / EtOAc 0-40% in 120 mm.) to give the title compound (3.33 g, 70%) as white solid, MS (ESI): mle = 198.1 [MHi.

The synthetic route of 185017-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FREI, Beat; GOBBI, Luca; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/86705; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1314353-68-8, 5-Cyclopropylpyridin-3-amine, 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, Quality Control of 5-Cyclopropylpyridin-3-amine, blongs to pyridine-derivatives compound. Quality Control of 5-Cyclopropylpyridin-3-amine

At 0 C, to a solution of 5-cyclopropylpyridin-3-amine (2.08 g, 15.49 minol) in tetrahydrofuran (30 mL) was added a solution of NaHMDS (6.84 g, 37.30 minol) in tetrahydrofuran (20 mL) dropwise over 10 min period. The resulting solution was stirred for 1 h at 0 C, and then was added by a solution of di-tert-butyl dicarbonate (4.85 g, 22.20 minol) in tetrahydrofuran (25 mL) dropwise. The resultingminxture was stirred for additional 2 h at room temperature. When the reaction was done, it was quenched by the addition of sat. NH4C1 solution (100 mL). The resultingminxture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with MeOH in EtOAc (0% to 80% gradient) to yield tert-butyl N-(5- cyclopropylpyridin-3-yl)carbamate as white solid (2.52 g, 69%). MS: m/z = 235.0 [M+Hj.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1314353-68-8, 5-Cyclopropylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

4.48 g (20 mmol) of the compound obtained in the preceding step in solution in 100 ml of diethyl ether and 9.05 ml (60 mmol) of tetramethylethylene-diamine are placed in a reactor, protected from moisture, and under a nitrogen atmosphere. After having cooled the solution to -70 C., 37.5 ml (60 mmol) of n-butyllithium in hexane (1.6 M) are added dropwise.. The reaction medium is stirred for 2 hours at -10 C. and then 14.1 g (60 mmol) of dihexyl sulfide are added dropwise at -70 C. After stirring the solution for 12 hours at room temperature, the reaction medium is taken up in water and extracted with diethyl ether.. The organic phase is washed with hydrochloric acid (0.1 M) and then with water until a PH of the washings equal to 7 is obtained, and then finally dried over sodium sulfate.. After evaporation of the solvent, an oil is obtained which is chromatographed on a silica gel (eluent ethyl acetate-hexane: 1-5).. After evaporation of the solvent, 5.6 g of an oil is obtained which crystallizes, that is to say a yield of 82.3%.. Its melting point is between 72 and 74 C. TLC: (MERCK “Kieselgel 60” silica gel; AcOEt-hexane: 1-3); Rf=0.3 I.R.: upsilon NH=3171, CO=1720; NMR: (CDCl3): 0.85 (t, 3H); 1.3 (m, 4H); 1.45 (m, 11H); 1.7-1.8 (m, 2H); 3.0 (t, 2H); 4.25 (s, 3H); 6.7 (d, 1H, J=6.8 Hz); 7.85 (d, 1H, J=6.8 Hz).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; US6339097; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 120739-77-7, 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 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine. This compound has unique chemical properties. The synthetic route is as follows.

1200 kg of dichloromethane was introduced into a 2000 L reactor, and 171 kg (1 kmol) of N-ethyl-2-chloro-5-pyridinemethylamine was added thereto with stirring, 60 L of ion exchange resin 201×7, and the mixture was cooled to an internal temperature of -10 C, and added dropwise. A solution of 157 kg (1.1 kmol) of 1-dichloro-2-nitroethylene and 320 kg of dichloromethane was added dropwise over 3 hours to control the internal temperature below 0 C. After the dropwise addition, the reaction was kept at 0 C for 3 hours. After the reaction is completed, a solution containing the compound (II) is obtained. The solution was further cooled to an internal temperature of -10 C, and slowly introduced into a methylamine gas of 46.5 kg, (1.5 kmol), controlled internal temperature of 0 C or less, and a calculated amount of monomethylamine gas was passed for 3 hours, and the temperature was maintained at 0 C. 3 hours. After completion, filtration, washing the ion exchange resin with dichloromethane, the filtrate is concentrated to dryness, adding 280 kg of ethyl acetate, stirring and crystallization at room temperature for 1 hour, then cooling to 0 C, stirring and crystallization for 3 hours, centrifuging the feed, drying to obtain the acetamid The amine was 252.3 kg, the purity was 99% or more, and the yield was 93%

According to the analysis of related databases, 120739-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Jinjing Chemical Co., Ltd.; Chen Xuejun; Ma Jun; Tang Songqing; (6 pag.)CN108822025; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

A microwave vial was charged with (iS,25)-l-A-(6-fluoro-l,3-beiizothiazol-2- yl)cyclopentane-l,2-di amine hydrochloride (Intermediate 1; 172 mg, 0.60 mmol), molybdenum hexacarbonyl (79 mg, 0.30 mmol), tri-tert-butylphosphonium (0587) tetrafiuoroborate (5 mg, 0.018 mmol), 2-bromo-3-(trifluoromethoxy)pyridine (145 mg, 0.60 mmol), Herrmanns Catalyst (6 mg, 6.41 muetaiotaomicron) and DBU (150 mu, 0.998 mmol) in dry 1,4-dioxane (2.4 ml). The reaction was subjected to microwave irradiation at 125 C for 25 minutes then partitioned between ethyl acetate and water. The organics were washed with water and brine, filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0 – 100% ethyl acetate / petrol then 0 – 30% methanol /’ ethyl acetate) then further purified by reverse phase preparative HPLC (eluted with acetonitriie / water containing 0.1 % ammonia) to afford the title compound. (0588) 1H NMR (400 MHz, DMSO-6) delta ppm 1.50 – 1.64 (m, 2 H), 1.68 – 1.80 (m, 2 1 1 }.. 2.07 – 2.21 (m, 2 H), 4.13 – 4.23 (m, 1 H), 4.23 – 4.33 (m, 1 H), 6.97 – 7.10 (m, 1 H), 7.26 – 7.37 (m, 1 H), 7.52 – 7.62 (m, 1 H), 7.64 – 7.74 (m, 1 H), 7.90 – 8.03 (m, 1 H), 8.14 – 8.23 (m, 1 H), 8.55 – 8.69 (m, 1 H), 8.92 – 9.02 (m, 1 H) MS ES?: 441

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Imidodicarbonic acid, 2-[5-bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , 1 -dimethylethyl) ester To 2-amino-5-bromonicotinonitrile (0.785 g, 3.96 mmol), triethylamine (0.553 mL, 3.96 mmol) and 4-dimethylaminoyridine (20 mg, 0.164 mmol) in CH2CI2 (25 mL) was added di-ferf-butyl- dicarbonate (2.16 g, 9.91 mmol) and the resulting mixture stirred at room temperature for 18h. Evaporated to dryness in vacuo and triturated in heptane (25 mL) for 72h. The resulting precipitate was filtered and washed with heptane (10 mL) to give imidodicarbonic acid, 2-[5- bromo-3-(cyano)-2-pyridinyl]-, 1 ,3-bis(1 , 1-dimethylethyl) ester as a beige solid (1.1 g, 70% yield). 1H N MR (400 Mhz, CDCI3, 298K) 1 .51 (s, 181-1) 8.16 (d, 1 1-1) 8.77 (d, 1 H). LCMS: [M+H]+=398/400.1 , Rt (4)= 1.43 min.

According to the analysis of related databases, 709652-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; COOKE, Nigel Graham; FERNANDES GOMES DOS SANTOS, Paulo; GRAVELEAU, Nadege; HEBACH, Christina; HOeGENAUER, Klemens; HOLLINGWORTH, Gregory; SMITH, Alexander Baxter; SOLDERMANN, Nicolas; STOWASSER, Frank; STRANG, Ross; TUFILLI, Nicola; VON MATT, Anette; WOLF, Romain; ZECRI, Frederic; WO2012/4299; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1198103-43-3, (6-(Difluoromethoxy)pyridin-3-yl)methanamine, 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, HPLC of Formula: C7H8F2N2O, blongs to pyridine-derivatives compound. HPLC of Formula: C7H8F2N2O

Phenyl formate (0.17 mL, 1.5 mmol) was added to a solution of (6- (difluoromethoxy)pyridin-3-yl)methylamine (0.261 g, 1.50 mmol) in dry dichloromethane (5 mL). The mixture was stirred at room temperature for 18 hours then the volatiles were removed in vacuo. The crude residue was purified by silica gel column chromatography using dichloromethane : methanol = 100:0 to 95:5 as gradient affording the title compound as white solid, 250 mg (82 %). 1H NMR (400 MHz, CDCl3) delta (ppm) 8.29 (s, 1 H) 8.12 (s, 1 H) 7.72 (d, 1 H) 7.45 (t, 1 H) 6.89 (d, 1 H) 5.81 (m, 1 H) 4.48 (d, 2 H). 19F NMR (400 MHz, CDCl3) delta (ppm) -89.30 and -89.49. MS (ESI) m/z 202 [M+H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1198103-43-3, (6-(Difluoromethoxy)pyridin-3-yl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2009/145720; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem