Category: 939412-86-9

Reference 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.

To a solution of 3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo[4,3-a]pyridine-7- carboxylic acid (1.63 g, 6.93 mmol) in THF (35 mL) was added dropwise (COCl)2 (4.4 g, 34.66 mmol) and 0.1 mL of DMF at 0 C, the mixture was stirred at this temperature for 1 hours and then the solvent was removed. The resulting residue was dissolved in THF (35 mL), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.37 g, 7.63 mmol) and DIEA(2.68 g, 20.79 mmol) was added, the mixture was stirred at 60 C for 1 h. Remove the solvent in vacuo and the residue was extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2S04. The organic layer was concentrated in vacuo and the residue was purified by silica gel column chromatography (DCM/THF= 100/20) to afford N-((3-chloropyrazin-2- yl)methyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-[l,2,4]triazolo [4,3-a]pyridine-7- carboxamide (0.8 g, yield 32%). MS-ESI (m/z): 361 (M+l) + (Acq Method: 10-80AB_2min;Rt: 0.81 min)

The synthetic route of 939412-86-9 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; LIU, Shilan; YANG, Chundao; ZHENG, Shuling; WO2014/113942; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

2a. Synthesis of N-((3-chloropyrazin-2-yl)methyl)-4-oxocyclohexanecarboxamide To a stirred suspension of 2-aminomethyl-3-chloropyrazine hydrochloride (3.89 mmol, 0.70 g) in dichloromethane (25 mL) at room temperature was subsequently added triethylamine (7.78 mmol, 1.08 mL), 0-(7-azabenzotriazol-1-yl)-1 ,1 ,3,3-tetramethyluroniumhexafluorophosphate (4.67 mmol, 1.77 g) and finally 4-oxocyclohexanecarboxylate (3.89 mmol, 553 mg). After stirring for 16 hours, the suspension filtered over decalite. The decalite was washed with dichloromethane. The filtrate was washed with water, dried (sodium sulfate) and concentrated in vacuo. The resulting crude product was purified by column chromatography on silica gel (ethyl acetate). The product was dissolved in dichloromethane, washed with water and concentrated in vacuo to afford 1.09 g of the title compound.H NMR (CDCl3, 400 MHz): delta 2.03 – 2.14 (m, 2H), 2.22-2.30 (m, 2H), 2.35 – 2.45 (m, 2H), 2.52 – 2.60 (m, 2H), 2.68 – 2.78 (m, 1 H), 4.73 (d, J = 4 Hz, 2H), 6.93 (brs, 1 H), 8.34 – 8.37 (m, 1 H), 8.46 (d, J = 2 Hz, 1 H).

Statistics shows that (3-Chloropyrazin-2-yl)methanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 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

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. Safety of (3-Chloropyrazin-2-yl)methanamine hydrochloride

trichloromethyl chloroformate (105 mmol, 12.68 mL) in tetrahydrofuran (100 mL) was cooled to 0 C and a solution of azetidine (88 mmol, 5 g) and N,N-diisopropylethylamine (193 mmol, 33.6 mL) in tetrahydrofuran (100 mL) was added slowly in 25 minutes. After stirring at 0 C for one hour the solids were removed by filtration and the filtrate was concentrated at 50 mbar (50C bath temperature). The residue was added to a solution of 2-aminomethyl-3-chloropyrazine hydrochloride (66.7 mmol, 12 g) and triethylamine (200 mmol, 27.9 mL) in dichloromethane (200 mL) and the reaction mixture was stirred for three hours. The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification using column chromatography (silica gel; gradient dichloromethane / methanol 100:0 to 95:5) yielded 9.5 g of N-((3-chloropyrazin-2-yl)methyl)azetidine-1-carboxamide.

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., COA of Formula: C5H7Cl2N3

The solution of 2- (5-chloro-2-isopropoxy-4-methyl-3- (6- (trifluoromethyl) pyridin-3-yl) phenyl) propanoic acid (680 mg, 1.6 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (366 mg, 2.56 mmol) , Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (1.25 g, 2.4 mmol) and N, N-Diisopropylethylamine (413 mg, 3.2 mmol) in DMF (10 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, brine and dried over Na 2SO 4, filtered and evaporated in vacuo to give the product (850 mg) which was used directly for the next step without further purification. MS (M+H) + 527.1, 529.1.

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

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

Electric Literature of 939412-86-9, These common heterocyclic compound, 939412-86-9, name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, 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.

2- (5-chloro-2-ethoxy-4-methyl-3- (6-methylpyridin-3-yl) phenyl) propanoic acid (2.7 g, 8.09 mmol) , (3-chloropyrazin-2-yl) methanamine hydrochloride (1.4 g, 9.71 mmol) , HOBt (1.32 g, 24.27 mmol) , EDCI (1.86 g, 9.71 mmol) and DIPEA (3.14 g, 24.27 mmol) were dissolved in THF (30 mL) and stirred at room temperature under N 2 for overnight, brine (20 mL) was added and extracted with ethyl acetate. The combined organic layers were washed with brine and dried over Na 2SO 4. The product (3.2 g in 86.1 %yield) was got. MS (ESI) m/e (M+1) +459.

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

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

Reference 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.

A mixture of SM (1.4 g, crude, 7.8 mmol), (3-chloropyrazin-2-yl)methanamine hydrochloride (1.4 g, 7.8 mmol), HATU (2.7 mg, 7.8 mmol) and TEA (3.2 mg, 31.2 mmol) in DCM (30 mL) was stirred at 25C overnight. The mixture was quenched with H20 (60 mL) and it was extracted with DCM (25 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product. The crude product was purified by prep- TLC to give 1 (1.3 g, 50 %). LCMS: m/z = 309 [M+H]+.

The synthetic route of (3-Chloropyrazin-2-yl)methanamine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LIAO, Xibin; SUZHOU BAIJIBUGONG PHARMACEUTICAL TECHNOLOGY CO. LTD.; LI, Jia; LU, Zhijian; ZHOU, Yubo; GAO, Anhui; (100 pag.)WO2018/175512; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, 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.

To a solution of 59 (3-chloropyrazin-2-yl)methanamine hydrochloride 1a (0.9 g, 5.0 mmol) and 32 N,N-dimethyl formamide (0.02 mL) in 25 dichloromethane (20 mL) at room temperature, was added dropwise a solution of 60 benzyl 3-(chlorocarbonyl)azetidine-1-carboxylate (1.3 g, 5.0 mmol) in dichloromethane (5.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with saturated 33 sodium bicarbonate solution (30 mL) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (30 mL×2). The combined organic phase was washed with saturated brine (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum and the residue was purified by flash column chromatography (20:1 dichloromethane/methanol) to provide 61 benzyl-3-(((3-chloropyrazin-2-yl)methyl)carbamoyl)azetidine-1-carboxylate 2a (1.20 g, 3.7 mmol, yellow oil). Yield: 75%.1H NMR (400 MHz, CDCl3) delta8.43 (d, J=2.4 Hz, 1H), 8.34 (d, J=2.4 Hz, 1H), 7.35-7.27 (m, 5H), 6.91 (bs, 1H), 5.10 (s, 2H), 4.71 (d, J=4.4 Hz, 2H), 4.27-4.19 (m, 4H), 3.40 (dd, J=6.0 & 6.0 Hz, 1H).

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

Reference:
Patent; GUANGZHOU INNOCARE PHARMA TECH CO., LTD.; KONG, Norman Xianglong; ZHOU, Chao; CHEN, Xiangyang; US2019/177333; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Related Products of 939412-86-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 939412-86-9 as follows.

To a mixture of (3-chloropyrazin-2-yl)methanamine hydrochloride (3.9 g, 21.8 mmol, leq) and (S)-l-((benzyloxy)carbonyl)piperidine-2-carboxylic acid (5.73 g, 21.8 mmol, 1.0 eq) in DCM (50 mL), was added TEA (12.1 mL, 87.2 mmol, 4.0 eq). The reaction mixture was cooled to 0 C. After 10 min, HATU (9.94 g, 26.2 mmol, 1.2 eq) was added, and the reaction mixture was stirred at 0 C for 1 h and then at room temperature overnight. The mixture was washed subsequently with 0.1 M HCl-solution, 5% NaHC0 ; water and brine. It was dried over anhydrous Na2S04, filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH=200: l – 50: 1) to afford the desired product 1 (7.13 g, yield 84.4 %). LCMS: m/z = 389 [M+H]+.

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; LIAO, Xibin; SUZHOU BAIJIBUGONG PHARMACEUTICAL TECHNOLOGY CO. LTD.; LI, Jia; LU, Zhijian; ZHOU, Yubo; GAO, Anhui; (100 pag.)WO2018/175512; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 939412-86-9, 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. 939412-86-9 name is (3-Chloropyrazin-2-yl)methanamine hydrochloride, This 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.

A 30 vial was charged with 8- (methoxycarbonyl) bicyclo [3.2.1] octane-3-carboxylic acid (830 mg, 3.91 mmol) , HATU (1784 mg, 4.69 mmol) , TEA (1.635 mL, 11.73 mmol) and DCM (20 mL) . The mixture was stirred at 30 for 30 minutes. Then (3-chloropyrazin-2-yl) methanamine hydrochloride (845 mg, 4.69 mmol) was added, the resulting mixture was stirred at 30 for 16 hours. The reaction mixture was diluted with EtOAc (50mL) and washed with brine (50mLx3) . The organic layer was evaporated to dryness and the residue was purified via combi flash (EtOAc in petroleum from 0to 50) to give the title compound. 1H NMR (400 MHz, CDCl3) : delta 8.46 (d, J 2.0 Hz, 1H) , 8.32 (brs, 1H) , 6.85 (brs, 1H) , 4.69-4.59 (m, 2H) , 3.72 (s, 3H) , 2.70-2.50 (m, 4H) , 2.05-1.93 (m, 2H) , 1.89-1.77 (m, 2H) , 1.70 (m, 2H) , 1.65-1.56 (m, 2H) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (3-Chloropyrazin-2-yl)methanamine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; KOZLOWSKI, Joseph A.; ANDRESEN, Brain M.; BOGA, Sobhana Babu; GAO, Xiaolei; GUIADEEN, Deodialsingh; CAI, Jiaqiang; LIU, Shilan; WANG, Dahai; WU, Hao; YANG, Chundao; (111 pag.)WO2016/106624; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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

Step 3: (7S.9aR)-benzyl 7-(((3-chloropyrazin-2-yl)methyl)carbamoyl)-4-oxohexahvdro-lH- pyridor 1.2-al pyrazine-2(6H)-carboxylate To a solution of (7R,9aS)-2-((benzyloxy)carbonyl)-4-oxooctahydro-lH-pyrido[l,2-a]pyrazine-7- carboxylic acid (480 mg, 1.444 mmol) in anhydrous DMF (10 mL) was added EDC (415 mg, 2.166 mmol), DMAP (265 mg, 2.166 mmol), (3-chloropyrazin-2-yl)methanamine, HCl (312 mg, 1.733 mmol), and TEA (0.302 mL, 2.166 mmol) under N2, and the mixture was stirred at 25 C for 12 hrs. The mixture was poured into H20 (150 mL), and extracted with EtOAc (20 mL chi 5). The organic layer was washed with H20 (10 mL chi 6), brine (30 mL), dried over Na2SC>4, filtered, and evaporated in vacuo to give the crude product, which was then purified by flash chromatography (DCM/THF=85 ~ 70 %) to afford the title compound. 1H NMR (400MHz CDC13) delta = 8.44 (d, J=2.0 Hz, 1H), 8.33 (s, 1H), 6.98 (br. s., 1H), 5.20 – 5.10 (m, 2H), 4.88 (d, J=12.9 Hz, 1H), 4.68 (d, J=3.9 Hz, 2H), 4.29 – 4.18 (m, 1H), 4.16 – 4.05 (m, 1H), 3.94 (br. s., 1H), 3.41 (br. s., 2H), 2.73 (t, J=12.3 Hz, 1H), 2.39 (t, J=11.7 Hz, 1H), 2.08 (d, J=11.3 Hz, 1H), 1.95 – 1.86 (m, 2H), 1.41 – 1.32 (m, 1H) ppm.

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

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