Category: 23611-75-8

These common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, 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. Quality Control of Methyl 6-chloropyrazine-2-carboxylate

Step 3: Preparation of (6-chloropyrazin-2-yl)methanol. To a solution of methyl 6- chloropyrazine-2-carboxylate (2.0 g, 11.6 mmol) in water (20 mL) at 0 C was added NaBH4 (2.3 g, 58.0 mmol) portionwise. The reaction mixture was warmed to r.t. and stirred for 30 mm, followed by addition of satd. aq. K2C03 (40 mL) and EtOH (20 mL). The resulting mixture was stirred for another 1 hr and extracted with EA (2 x 20 mL). The combined organic layers were dried over anhydrous Na2SO4and concentrated and purified by standard methods to afford (6- chloropyrazin-2-yl)methanol. LC-MS: m/z 145.0 (M+H).

The synthetic route of Methyl 6-chloropyrazine-2-carboxylate has been constantly updated, and we look forward to future research findings.

Electric Literature of 23611-75-8, These common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, 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.

Example 12; 6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-methylbenzyl)pyrazine-2-carboxamide; Example 12A; 6-Chloro-pyrazine-2-carboxylic Acid 2-methyl-benzylamide; The product from Example 1E (1.00 g, 5.79 mmol) and MgCl2 (1.11 g, 11.7 mmol) were suspended in THF (25 mL) and stirred at ambient temperature for 5 min. 2-Methylbenzylamine (1.8 mL, 14.5 mmol) was added, and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with water (150 mL) and extracted with CH2Cl2 (4×100 mL). The organic extracts were combined and washed with 0.25M HCl (aq) (100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography to afford the title compound as a white solid (1.35 g, 89%). 1H NMR (DMSO-d6, 300 MHz) delta ppm 2.33 (s, 3H), 4.48 (d, J=6.10 Hz, 2H), 7.12-7.26 (m, 4H), 9.02 (s, 1H), 9.15 (s, 1H) 9.33 (t, J=5.76, 1H). MS (DCI/NH3) m/z 262 (M+H)+.

The synthetic route of 23611-75-8 has been constantly updated, and we look forward to future research findings.

23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, belongs to pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C6H5ClN2O2

Example 1F; (3aR,6aS)-tert-butyl 5-(6-(methoxycarbonyl)pyrazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate; The product from Example 1E (1.74 g, 10.08 mmol) was dissolved in DMSO (10 mL). The product from Example 1C (2.29 g, 10.79 mmol) and sodium carbonate (1.61 g, 15.19 mmol) were added to the reaction mixture. The reaction was stirred at 120 C. for 16 h. The reaction was then allowed to cool to ambient temperature, diluted with water (100 mL) and extracted with CH2Cl2 (4×100 mL). The organic extracts were combined and washed with water (100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc, Rf=0.36) to afford the title compound as a thick oil that slowly solidified (2.78 g, 78%). MS (DCI/NH3) m/z 349 (M+H)+.

The synthetic route of 23611-75-8 has been constantly updated, and we look forward to future research findings.

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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below. Product Details of 23611-75-8

Step 1. Methyl 6-(5-chloro-l-[f4-methylphenyl)sulfonyll-lH-pyrrolo[2 -&]pYridin-3-Yl}- pyrazine-2-carboxylateA solution of methyl 6-chloropyrazine-2-carboxylate (0.1 g, 0.579 mmol), 5- chloro- 1 -[(4-methylphenyl)sulfonyl]-3-(4s4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)- 1H- pyrrolo[2,3-&]pyridine (0.276 g, 0.637 mmol), PdCl2(dppf) (0.085 g, 0.116 mmol) and Na2C(¾(0.87 mL, 2 M in water, 1.74 mmol) in DMF (6 mL) was microwaved at 130 C for 20 min. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was then washed with 1/2 brine and brine before dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of ethyl acetate: hexane 10:90 to 80:20 to afford the title compound. MS APCI: [M + H]+ m/z = 443.0.

The synthetic route of 23611-75-8 has been constantly updated, and we look forward to future research findings.

Electric Literature of 23611-75-8,Some common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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 stirring solution of methyl 6-chloropyrazine-2-carboxylate (2.50 g, 14.49 mmol) in THF (50 mL) was added methylmagnesium bromide 3M in diethyl ether (12.07 mL, 36.2 mmol) at 0 C. The resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was diluted with saturated NH4Cl (100 mL) and extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (Redisep-24 g, 0.40 % EtOAc/n-hexane) to obtain Intermediate 105A (0.70 g, 28.00%). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.44 (s, 6 H), 5.58 (br,s 1 H), 8.66 (s, 1 H), 8.86 (s, 1 H). LCMS: The compound did not ionize well.

The synthetic route of 23611-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 23611-75-8,Some common heterocyclic compound, 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, molecular formula is C6H5ClN2O2, 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.

6-((2-Chloro-5-nitrobenzyl)oxy)pyrazine-2-carboxamide (IE3) An oven-dried seal tube was charged with Pd(OAc)2 (4.4 mg, 0.02 mmol, 1 mol %), t-Bu-Xphos (17 mg, 0.04 mmol, 2 mol %) and Cs2CO3 (980 mg, 3.0 mmol, 1.5 equiv). The seal tube was sealed with a septum, evacuated and back-filled with argon. Toluene (10 mL), methyl 6-chloro-2-pyrazinecarboxylate (IE2, 340 mg, 2.0 mmol), and 2-chloro-5-nitrobenzyl alcohol (IE1, 1.13 g, 6.0 mmol) were added via syringe. The reaction mixture was heated at 100 C. for 24 h, then cooled to room temperature, diluted with EtOAc (20 mL), filtered through a pad of Celite, and concentrated. The residue was purified by flash column chromatography (0-50% EtOAc/hexanes) to afford an inseparable mixture of IE1 and the coupling product. This mixture in NH3/MeOH (ca. 7 N, 20 mL) in a seal tube was heated at 70 C. for 24 h. After the solvent was evaporated in vacuo, the residue was dissolved in EtOAc (150 mL) and the resulting solution was washed with H2O (150 mL) and brine (100 mL). After the organic layer was dried over Na2SO4 and filtered, the filtrate was concentrated and the residue was purified by flash column chromatography (0-15% MeOH/CH2Cl2) to afford compound IE3 as a light yellow solid (100 mg, 16% over two steps). 1H NMR (CDCl3, 600 MHz) delta 9.06 (s, 1H), 8.60 (s, 1H), 8.47 (d, J=2.4 Hz, 1H), 8.19 (dd, J=9.0, 2.4 Hz, 1H), 7.63 (d, J=9.0 Hz, 1H), 5.59 (s, 2H). HRMS (ESI+) calcd for C12H10ClN4O4 (M+H)+ 309.0385, found 309.0392.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 6-chloropyrazine-2-carboxylate, its application will become more common.

Reference:
Patent; REGENTS OF THE UNIVERSITY OF MINNESOTA; Chen, Liqiang; Ai, Teng; More, Swati; (111 pag.)US2016/376238; (2016); 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. 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 6-chloropyrazine-2-carboxylate

A mixture of l-(4-((4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)methyl)benzyl)pyridin-2(lH)-one (339 mg, 1.05 mmol, 3.0 eq), methyl 6-chloropyrazine-2-carboxylate (150 mg, 0.87 mmol, 1.0 eq), Pd(dppf)Ci2 (71 mg, 0.061 mmol, 0.1 eq), K2C03 (240 mg, 1.74 mmol, 2.0 eq) in toluene/dioxane/H20 (10 niL/1 niL/1 mL) under N2 was stirred at 100 C for 5 h and then concentrated. The residue was extracted with EA (50 mL X 3). The combined organic layers were dried over anhydrous sodium sulfate and concentrated. The residue was purified via pre-TLC to afford methyl 6-(4-((2-oxopyridin-l(2H)-yl)methyl)benzyl)pyrazine-2-carboxylate as a white solid (100 mg, 34%).

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 23611-75-8.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

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 23611-75-8 as follows. Formula: C6H5ClN2O2

A suspension of methyl 6-chloropyrazine-2-carboxylate (3.4 g, 19.7 mmol) in THF (100 mL) was cooled to below 10 C and treated dropwise with 3M MeMgBr (Et20, 13.13 mL, 39.4 mmol), maintaining the reaction temperature below 10 C. The reaction mixture was then allowed to warm to RT. After 1 hr, the reaction mixture was concentrated then taken up in 1M HCI (aq, 150 mL) and extracted with EtOAc (3 x 70 mL). The organic layers were combined, dried (Mg504), filteredand concentrated on to silica (4 g). The crude product was purified by chromatography on silica gel (40 g column, 20-70% EtOAc/iso-hexane) to afford 2-(6-chloropyrazin-2-yl)propan-2-ol (1 .4 g, 7.71 mmol, 39% yield) as an orange oil; Rt 1.30 mins (HPLC acidic); mlz 173 (M+H) (ES); 1H NMR (500 MHz, DMSO-d6) 6 8.87 (d, J = 0.5 Hz, 1 H), 8.67 (d, J = 0.5 Hz, 1 H), 5.61 (s, 1 H), 1.46 (s, 6H).

According to the analysis of related databases, 23611-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STEP PHARMA S.A.S.; QUDDUS, Abdul; NOVAK, Andrew; COUSIN, David; CHATZOPOULOU, Elli; BLACKHAM, Emma; JONES, Geraint; THOMAS, Jennifer; WRIGGLESWORTH, Joseph; DUFFY, Lorna; BIRCH, Louise; GEORGE, Pascal; AHMED, Saleh; (277 pag.)WO2019/106156; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

A common compound: 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 23611-75-8

Step 1 :Preparation of6-(6-chloropyrazin-2-yl)-N2,N?-bis (4,4-dfluorocyclohexyl)-1,3,5-triazine-2,4-diamine. To a mixture of methyl 6-chloropyrazine-2-carboxylate (300mg, 1. 74mmol) and N?,N5-di-(4,4-difluorocyclohexanamine)- biguanide (700 mg, 2.10 mmol)in MeOH (8 mL) was added MeONa (340 mg, 6.28 mmol).The reaction mixture was stirred at r.t. overnight, and then partitioned between EtOAc (30 mL) and 1120(3OmL). The organic layerwas separated, washed with brine (30 mL), dried over anhydrous Na2SO4, and concentrated and purified by standard methods to afford the desired product. ?H NIVIR (400MHz, DMSO-d6) 9.48 – 9.32 (m, 111), 8.93 (d,J811z, 111), 7.92 – 7.59 (m, 211), 4.15 -3.95(m, 211), 2.08 – 1.60(m, 1611).LCMS:m/z 460(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, 23611-75-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; KONTEATIS, Zenon D.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; ZAHLER, Robert; CAI, Zhenwei; ZHOU, Ding; WO2015/3640; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

23611-75-8, A common compound: 23611-75-8, name is Methyl 6-chloropyrazine-2-carboxylate, belongs to Pyrazines compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 66Methy[ 6- ({4-[(3,4-dif[uoropheny[)carbamoy[]-3-methy[- 1 ,2-thiazo[-5-y[lamino)-pyrazine-2-carboxy[ate A mixture of 5-amino-N-(3,4-dif[uoropheny[)-3-methy[-1 ,2-thiazo[e-4-carboxamide [Intermediate 3] (150 mg, 0.56 mmo[, 1.0 eq), methy[ 6-ch[oropyrazine-2- carboxy[ate [CAS RN: 23611-75-8] (120 mg, 0.56 mmo[, 1.0 eq) and cesiumcarbonate (417 mg, 1.28 mmo[, 2.3 eq) in 5.4 mL dioxane/DMF (7/1) was p[aced ina microwave via[ and f[ushed with argon. Then, pa[[adium(II) acetate (13 mg,0.06 mmo[, 0.1 eq) and Xantphos (32 mg, 0.06 mmo[, 0.1 eq) were added. The via[was capped and the reaction mixture was stirred at an environmenta[ temperatureof 110 C overnight. On coo[ing, the vo[ati[e components were removed in vacuo.The crude materia[ was disso[ved in a sma[[ amount DM50 and fi[tered. Purificationwas conducted via preparative HPLC (method A) to give 10 mg (4 % yie[d of theory) of the tit[e compound.UPLC-MS (Method 1): R = 1.20 mm; MS (ESIneg) m/z = 404 [M-H].1H-NMR (400 MHz, DMSO-d6): oe [ppm] = 3.98 (s, 3H), 7.38-7.53 (m, 2H), 7.95 (m,1H), 8.73 (s, 1H), 8.84 (s, 1H), 10.48 (s, 1H), 11.22 (s br, 1H), 1xCH3 not assigned.

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, Methyl 6-chloropyrazine-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; PRECHTL, Stefan; SIEMEISTER, Gerhard; WENGNER, Antje Margret; ACKERSTAFF, Jens; NOWAK-REPPEL, Katrin; BADER, Benjamin; LIENAU, Philip; STOeCKIGT, Detlef; WO2014/118186; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem