Category: 939412-86-9

Reference of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

2-Chloro-3-aminomethylpyrazine HCl (2 g; 11.1 minol), (5)-(-)-l-(carbobenzyloxy)-2- piperidine carboxylic acid (3.2 g; 12.2 minol) and N,N-diisopropylethylamine (7.7 mL; 44.4 minol) were dissolved in dichloromethane (100 mL). N-[(dimethylamino)-lH-l,2,3-triazolo- [4,5-6]pyridin-l -ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide (HATU) (6.3 g; 16.7 minol) was added and the resulting mixture was stirred overnight at room temperature. The mixture was washed with aqueous sodium bicarbonate solution and water. The organic layer was then dried over sodium sulfate, filtered and evaporated to dryness. The crude material was chromatographed over S1O2 using a gradient of 20 -80% ethyl acetate in heptane to give 4.4 g; 11.3 minol of benzyl (2Patent; ACERTA PHARMA B.V.; BARF, Tjeerd; KAPTEIN, Allard; VERKAIK, Saskia; DEMONT, Dennis; COVEY, Todd; VAN DE KAR, Bas; VAN LITH, Bart; GULRAJANI, Michael; (166 pag.)WO2018/134786; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, The chemical industry reduces the impact on the environment during synthesis 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, I believe this compound will play a more active role in future production and life.

(3-chloropyrazin-2-yl)methanamine.hydrochloride (5 g, 27.8 mmol) and triethylamine (11.61 mL, 83 mmol) dichloromethane (80 mL) was added acetic anhydride (2.63 mL, 27.8 mmol) and the reaction mixture was stirred at 0C for 30 min. The mixture was filtered and the filtrate concentrated in vacuo. The product was purified using silica gel chromatography (ethylacetate/ethanol = 5/1 v/v%) to give 4.45 g of N-((3-chloropyrazin-2-yl)methyl)acetamide (88%).

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, (3-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

A mixture of (cis)-2-((benzyloxy)carbonyl)-4-oxooctahydro-1H-pyrido[1,2-a]pyrazine-7-carboxylic acid (0.7 g, 2.1 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (450 mg, 2.5 mmol), HATU (1.2 g, 3.1 mmol) and TEA (0.85 g, 8.4 mmol) in DMF (10 mL) was stirred at 25 C. for overnight. Then the reaction mixture was poured into water, the mixture was extracted with EA (50 ml*3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4, concentrated in vacuo, the residue was purified by silica gel column chromatography (PE/THF=1/3) to give (cis)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahydro-1H-pyrido[1,2-a]pyrazine-2(6H)-carboxylate (440 mg, yield 45.8%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (3-Chloropyrazin-2-yl)methanamine hydrochloride, its application will become more common.

Reference:
Patent; KIM, RONALD M.; Liu, Jian; Gao, Xiaolei; Boga, Sobhana Babu; Guiadeen, Deodialsingh; Kozlowski, Joseph A.; Yu, Wensheng; Anand, Rajan; Yu, Younong; Selyutin, Oleg B.; Gao, Ying-Duo; Wu, Hao; Liu, Shilan; Yang, Chundao; Wang, Hongjian; US2014/206681; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 939412-86-9

in a 3 L reaction flask, DCM (dichloromethane) (500 mL), intermediate 2 (39 g,217 mmol), 1148-11-4 (N-benzyloxycarbonyl-L-proline) (54 g, 217 mmol) and Et3N (87.7 g, 868 mmol) were addedsuccessively. Under nitrogen protection, the reaction solution was cooled to 0 C and HATU (2-(7-azobenzotriazole)-tetramethylurea hexafluorophosphate) (98.8 g, 260 mmol) was added in batches. The reaction solution wasnaturally warmed to room temperature, and the reaction was carried out for 14 hours under stirring. After the reactionwas completed, HCl (400 mL, 0.5 N H2O) was added, the obtained mixture was filtered through diatomite and wasextracted, the organic phase was washed with NaHCO3 (5%) and saturated saline solution, dried over Na2SO4 andconcentrated, then passed through column (PE (polyethylene): EA (ethyl acrylate) = 1:1) to obtain intermediate 3(12.7 g, yield: 14.7%) as a white solid. LCMS showed a molecular ion peak (M+1) 375.0.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Hangzhou Sanyintai Pharmaceutical Technology Co., Ltd.; Yin, Jianming; YIN, Jianming; LV, Yubin; LI, Bangliang; (36 pag.)EP3480199; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 939412-86-9, A common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

Intermediate 12. Step 12: N-((3-chloropyrazin-2-yl)methyl)-2.3.3-trimethyl-l-oxooctahvdro-lH-pyrido[1.2- clpyrimidine-7-carboxamide (trans) To a solution of 2,3,3-trimethyl-l -oxooctahydro-lH-pyrido[l ,2-c]pyrirnidine-7-carboxylic acid (560 mg, 2.330 mmol) in DMF (25 mL) was added HATU (1329 mg, 3.50 mmol), the mixture was stirred at 20 C for 0.5 h. Then (3-chloropyrazin-2-yl)methanamine,HCl (503 mg, 2.80 mmol) was added, followed by Epsilon Nu (1.299 mL, 9.32 mmol). The mixture was stirred at 20 C – I l l – for 18 h. TLC showed the material was consumed completely, then the reaction mixture was poured into water (20 mL), extracted with DCM (20 mLx2). The organic layer was washed with brine (40 mL), dried over Na2SC>4, concentrated in vacuo to give N-((3-chloropyrazin-2- yl)methyl)-2,3,34rimethyl-l-oxooctahydro-lH-pyrido[l,2-c]pyrirnidine-7-carboxamide (trans) . XH NMR (400MHz, CD3OD) delta 8.52 (d, J = 2.3 Hz, 1H), 8.33 (s, 1H), 4.62 (s, 2H), 4.56 (d, J = 12.9 Hz, 1H), 3.26 – 3.21 (m, 1H), 2.86 (s, 3H), 2.65 (t, J= 12.3 Hz, 1H), 2.43 (t, J= 11.7 Hz, 1H), 2.03 – 1.82 (m, 4H), 1.67 (br. s., 1H), 1.31 (s, 3H), 1.29 – 1.24 (m, 1H), 1.21 (s, 3H) ppm.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph, A.; ALHASSAN, Abdul-Basit; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; WANG, Jyhshing; XU, Jiayi; YU, Wensheng; YU, Younong; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (211 pag.)WO2016/109221; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9,Some common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, molecular formula is C5H7Cl2N3, 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.

(3-chloropyrazin-2-yl)methanamine.hydrochloride (1.85 g, 10.28 mmol), (R)-piperidine-1,3-dicarboxylic acid 1-benzylester (2.71 g, 10.28 mmol) and HATU (4.1 g, 10.79 mmol) in dichloromethane (75 mL) was added triethylamine (5.73 mL, 41.1 mmol) and the reaction mixture was stirred at 0C for 4 hr. and after warming up to room temperature over night. The mixture was washed with 0.1 M HCl-solution, 5% NaHCO3, water and brine, dried over sodium sulfate and concentrated in vacuo to give 5.03 g of crude (R)-benzyl 3-((3-chloropyrazin-2-yl)methylcarbamoyl)piperidine-1-carboxylate (126%) which was used directly in the next step.

The synthetic route of 939412-86-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MSD Oss B.V.; Man, de, Adrianus, Petrus, Antonius; Sterrenburg, Jan-Gerard; Raaijmakers, Hans C.A.; Kaptein, Allard; Oubrie, Arthur A.; Rewinkel, Johannes, Bernardus, Maria; Jans, Christiaan, Gerardus, Johannes, Maria; Wijkmans, Jacobus C.H.M.; Barf, Tjeerd A.; Gao, Xiaolei; Boga, Sobhana Babu; Yao, Xin; Zhu, Hugh Y.; Cooper, Allen B.; Kim, Ronald M.; EP2548877; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 939412-86-9

The reaction mixture of 2- (5-chloro-4-fluoro-2-isopropoxy-3- (6- (trifluoromethyl) pyridin-3-yl) phenyl) propanoic acid (520 mg, 1.28 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (293 mg, 2.05 mmol) , Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (998 mg, 1.92 mmol) and N, N-Diisopropylethylamine (330 mg, 2.56 mmol) in DMF (20 mL) was stirred at room temperature for overnight. After completed, the solvent was evaporated in vacuo and the residue was dissolved with ethyl acetate. The mixture was washed with water and brine, dried over Na 2SO 4, filtered and evaporated in vacuo to give the product which was used directly for the next step without further purification. MS (M+H) + 531.1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BEIGENE, LTD.; LI, Jing; ZHAO, Haibo; WANG, Zhiwei; (193 pag.)WO2018/103688; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 939412-86-9, 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. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

(2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-(hydroxymethyl) morpholine-4-carboxylate (2g, 4.12 mmol) was dissolved in 100 mL CH2Cl2and cooled to 0 C. TEMPO(0.13 g, 0.82 mmol) was added, followed by (diacetoxyiodo)benzene (2.65 g, 8.24 mmol). The ice bath was removed, and the reaction was allowed to warm to room temperature and stirred overnight. The mixture was diluted with 200 mL ethyl acetate and washed with 10% Na2S203, aq. satd. NaHC03, and brine. The organic phase was dried with Na2S04, filtered and concentrated to give (2R,5R)-4-(tert- butoxycarbonyl)-5 -(((tert-butyl diphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.36g, 66%). LCMS: [M-H]+:498.23 Ret. time= 1.33 min, LC-MS method E). Used as such for the next step without any further purification. (2R,5R)-4-(tert-butoxycarbonyl)-5-(((tert- butyldiphenylsilyl)oxy)methyl)morpholine-2-carboxylic acid (1.5g, 3.0 mmol) and (3- chloropyrazin-2-yl)methanamine. HC1 salt (0.54g, 3.0 mmol) were dissolved in DMF 100 mL. To the reaction mixture was added Et3N (0.76g, 6.0 mmol) followed by slow addition of HATU (1.37g, 3.6 mmol) at 0 C. The reaction was stirred at rt for 1 day under a stream of nitrogen and then quenched with sat. NaHC03 (100 mL) and extracted with EtOAc(2xl50 mL). The combined organic layer was washed with water(200 mL) , brine(200mL), dried over anhydrous Na2S04, filtered, and evaporated. The crude residue was subjected to column purification using 20-50%) EtO Ac/Hex. to give (2R,5R)-tert-butyl 5-(((tert-butyldiphenylsilyl)oxy) methyl)-2-(((3-chloropyrazin- 2-yl)methyl)carbamoyl)morpholine-4-carboxylate (0.86g, 46%). LCMS: [M-Boc +H]+:525.25 Ret. time= 2.74 min, LC-MS method E).

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, (3-Chloropyrazin-2-yl)methanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

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;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (3-Chloropyrazin-2-yl)methanamine hydrochloride

2-Aminomethyl-3-chloropyrazine hydrochloride (content 77%; 34.7 mmol, 6.47 g), trans-4- hydroxycyclohexanecarboxylic acid (34.7 mmol, 5 g), N,N-diisopropylethylamine (104 mmol, 18.12 ml, 13.45 g), 4-dimethylaminopyridine (3.47 mmol, 0.424 g) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide) hydrochloride (45.1 mmol, 8.64 g) in dichloromethane (100 ml) were stirred at room temperature. After 16 hours the reaction mixture was diluted with 2N hydrochloric acid and extracted with dichloromethane three times. The organic layer was dried (sodium sulfate) and concentrated in vacuo. The crude product was triturated with dichloromethane to give 2 g of solid (trans)-N-((3-chloropyrazin-2- yl)methyl)-4-hydroxycyclohexanecarboxamide. The mother liquor was dissolved in ethyl acetate and washed with aqueous sodium hydrogencarbonate solution, dried (sodium sulfate) and concentrated to give an additional crop of 0.7 g of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 939412-86-9.

Reference:
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 939412-86-9

(3-Chloropyrazin-2-yl)methanamine hydrochloride (157 mg, 0.873 mmol), 2-chloro-4- methoxyphenylboronic acid (325 mg, 1.75 mmol), potassium carbonate (482 mg, 3.49 mmol) and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.043 mmol) in water (1.5 mL) and DME (4.5 mL) was microwave irradiated at 110 C for 30 min. After organic solvent was removed in vacuo, the residue was extracted with EtOAc and washed successively with water and brine. The organic layer was dried over Na2S04and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (MeOH/DCM) to obtain 64 mg of [3-(2-chloro-4-methoxy- phenyl)-pyrazin-2-yl]-methylamine.

According to the analysis of related databases, 939412-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF WASHINGTON; FAN, Erkang; ZHANG, Zhongsheng; HUANG, Wenlin; BUCKNER, Frederick S.; (180 pag.)WO2018/237349; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem