Category: 36070-80-1

Electric Literature of 36070-80-1, The chemical industry reduces the impact on the environment during synthesis 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, I believe this compound will play a more active role in future production and life.

Using general method 3 (step 1), trans intermediate 19 (150 mg, 0.354 mmol) and 5-chloropyrazine-2-carboxylic acid (67.4 mg, 0.425 mmol) were combined to afford the title compound (140 mg, 0.248 mmol, 70.1%) as a white solid. MS m/z=564.0 (M+H). To the crude tert-butyl ((11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (190 mg, 0.449 mmol) from Step 4 (-2:1 trans/cis mixture) dissolved in DMF (2 ml), was added 5-chloro-3-methylpyridine-2-carboxylic acid (92 mg, 0.538 mmol), pyridine (0.109 ml, 1.346 mmol) and HATU (256 mg, 0.673 mmol) and resulting solution was stirred for 1 hr at RT. The mixture was diluted with EtOAc (8 ml) and saturated NaHCO3 solution (3 ml). Water was added to dissolve precipitated solids. The organic layer was separated, washed with water, brine and concentrated. The residue was and purified by silica gel chromatography on 12 g RediSep Gold column using 10-70% EtOAc in heptane to afford major less polar trans-isomer tert-butyl ((4aR,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (110 mg, 0.191 mmol, 42.5% yield and more polar minor cis-isomer tert-butyl ((4aS,11bR)-10-(5-chloro-3-methylpicolinamido)-3,3,11b-trimethyl-4,4-dioxido-4-a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (70 mg, 0.121 mmol, 27% yield).

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, 5-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, A common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 56 2 (R)- (3-CHLORO-4-METHANESULFONYL-PHENYL)-3-CYCLOPENTYL-N- [5- (2-HYDROXY-1- HYDROXYMETHYL-ETHOXY)-PYRAZIN-2-YL]-PROPIONAMIDE [000288] A suspension of 5-chloro-pyrazine-2-carboxylic acid (prepared as in Example 29,1. 00 g, 6.33 mmol) in methylene chloride (30 mL) was treated with 1,3- dibenzyloxy-2-propanol (2.06 g, 7.57 MMOL), bis (2-oxo-3-oxazolidinyl) phosphinic chloride (1.61 g, 6.34 mmol), and triethylamine (1.83 mL, 12.66 mmol). The mixture was stirred at 25C overnight. The solution was extracted with methylene chloride and a saturated sodium bicarbonate solution. The organic layer was washed with water, a saturated aqueous sodium chloride solution, a 1N hydrochloric acid solution and a saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40L, Silica, 3/1 hexanes/ethyl acetate) afforded the 5-chloropyrazine-2-carboxylic acid 2- BENZYLOXY-1-BENZYLOXYMETHYL-ETHYL ester (1.45 g, 55.7%) as a colorless oil.

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; F. HOFFMANN-LA ROCHE AG; WO2004/52869; (2004); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., SDS of cas: 36070-80-1

To a 0 C mixture of 5-chloropyrazine-2-carboxylic acid (1.0 g, 6.31 mmol) in DCM (6.3 mL) was added oxalyl chloride (6.3 mL, 12.6 mmol) and several drops of (0965) DMF. The mixture was stirred at RT overnight, then was concentrated in vacuo to provide the title compound, which was used in the next step without further purification.

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; BRISTOL-MYERS SQUIBB COMPANY; CHENG, Peter Tai Wah; SHI, Yan; KALTENBACH, Robert F. III; WANG, Ying; ZHANG, Hao; (160 pag.)WO2019/126099; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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 5-chloropyrazine-2-carboxylic acid (3 g, 18.9 mmol) in dichloromethane (60 mL) was added oxalyl dichloride (2.52 g, 1.7 mL, 19.9 mmol) dropwise at 0C. Then to the mixture was added 2 drops of DMF and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was concentrated in vacuo to give 5- chloropyrazine-2-carbonyl chloride (3.4 g, 100%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; SHEN, Hong; TAN, Xuefei; WU, Jun; CHEN, Dongdong; LI, Chao; WANG, Li; (156 pag.)WO2020/53249; (2020); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

Step 1: 5-chloro-N-[l-(trifluoromethyl)cyclopropyl]pyrazine-2-carboxamideN,N-Diisopropylethylamine (1.3 niL, 7.5 mmol) was added to a mixture of 5- chloropyrazine-2-carboxylic acid (0.40 g, 2.5 mmol), N,N,N’,N’-tetramethyl-0-(7- azabenzotriazol-l-yl)uronium hexafluorophosphate (1.0 g, 2.8 mmol) and 1- (trifluoromethyl)cyclopropanamine (0.32 g, 2.5 mmol) (Oakwood, Cat.No.: 038175) in dichloromethylene (10 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was worked up with saturated aqueous NaHCCh, and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with brine, dried over MgS04, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-20%) to afford the desired product (0.41 g, 67%). LCMS (M+H) +: m/z = 266.0/267.9.

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; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 36070-80-1

Oxalyl chloride (1.55 ml, 17.48 mmol), followed by DMF (2 drops), was added to a mixture of 5-chloropyrazine-2-carboxylic acid (2.31 g, 14.57 mmol) in DCM (40 ml). The reaction was stirred at RT for 2 hours after which time the volatiles were removed in vacuo. The residue was taken up DCM (40 ml) and azetidine (1.08 niL, 16.03 mmol) and triethylamine (4.46 ml, 32.06 mmol) added. The mixture was stirred at RT for 72 hours. The volatiles were removed in vacuo and ethyl acetate (100 ml) added to the residue. The organics were washed with water (100 ml), citric acid (50 ml), saturated sodium bicarbonate solution (50 ml), brine (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow solid. The residue was chromatographed on silica, EPO eluting with a gradient of 50 -100% ethyl acetate in o-hexane, to give the desired compound as a yellow solid (2.38 g), 1H NMR delta (CDCl3): 2.35 – 2.42 (2H, m), 4.26 (2H, t), 4.67 (2H, t), 8.52 (IH, d), 9.09 (IH, d); m/z 198 (M+H)+.

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 36070-80-1.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125958; (2006); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, belongs to Pyrazines compound, 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 36070-80-1, HPLC of Formula: C5H3ClN2O2

50 ml RBF was charged with 3-pentyn-2-ol (2.063 ml, 22.08 mmol) in DMF (10 ml) and potassium t-butoxide (1.24 g, 11.04 mmol) was added portionwise while stirring (cooling in water bath). The mixture was stirred at room temperature for 10 min until all t-BuOK went into solution, then 5-chloropyrazine-2-carboxylic acid (500 mg, 3.15 mmol) was added in portions and the resulting brown suspension was heated at 75 C. for 45 min. The mixture was cooled to room temperature and diluted with water (20 ml) until all solids dissolved, then acidified with 2M HCl solution (5.5 ml) to pH 2. The resulting solution was extracted with EtOAc, organic layer was washed with water twice then with brine, filtered through pad of celite and concentrated in vacuo. The resulting suspension was diluted with 3 ml heptane/EtOAc (20:1) mixture then filtered. The solid was washed with heptane and dried in vacuo to afford 5-(pent-3-yn-2-yloxy)pyrazine-2-carboxylic acid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloropyrazine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; WHITE, Ryan; ALLEN, Jennifer R.; EPSTEIN, Oleg; HONG, Fang-Tsao; HUA, Zihao; HUMAN, Jason Brooks; LOPEZ, Patricia; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; TAMAYO, Nuria A.; ZHENG, Xiao Mei; US2014/213581; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1, 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 36070-80-1 as follows.

5-(Oxetan-2-ylmethoxy)pyrazine-2-carboxylic acid In a microwave vial 5-chloropyrazine-2-carboxylic acid (100.0 mg, 0.631 mmol), dimethylformamide (5 mL), oxetan-2-ylmethanol (83.4 mg, 0.946 mmol) and potassium tert-butoxide (176.9 mg, 1.58 mmol) are added. A small exotherm is observed. After 1 minute at room temperature the vial is sealed and the mixture heated at 120 C. for 30 minutes in the microwave. The reaction mixture is then quenched with aqueous NH4Cl and the solvent evaporated under reduced pressure. The resultant residue is triturated in 2-propanol. The filtrate is concentrated under reduced pressure to give the title compound as a cream solid (0.294 g, 99%) and is used without further purification. ES/MS (m/e): 211.0 (M+1), 208.8 (M-H).

According to the analysis of related databases, 36070-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GREEN, Steven James; HEMBRE, Erik James; MERGOTT, Dustin James; SHI, Yuan; WATSON, Brian Morgan; WINNEROSKI, JR., Leonard Larry; US2014/371212; (2014); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 36070-80-1,Some common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

5-Chloropyrazine-2-carboxylic acid (27, 7.84 g), N,N-dimethylformamide(120 mL), ethyl piperidine-4-carboxylate (16.0 mL),and N,N-diisopropylethylamine (25.0 mL) were mixed, followed bystirring at 90 C for 8 h. The reaction mixture was cooled to roomtemperature and ethyl acetate was added. The mixture was washedwith a dilute hydrochloric acid solution and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration andthe filtrate was concentrated under reduced pressure. The obtainedsolid was washed with diisopropyl ether and dried to obtain 28 (6.80 g,49%) as a milky white solid: 1H NMR (CDCl3) delta 1.27 (3H, t,J = 7.0 Hz), 1.74-1.86 (2H, m), 2.02-2.11 (2H, m), 2.66 (1H, tt,J = 10.5, 4.1 Hz), 3.20-3.30 (2H, m), 4.17 (2H, q, J = 7.1 Hz),4.33-4.42 (2H, m), 8.02 (1H, d, J = 1.3 Hz), 8.86 (1H, d, J = 1.3 Hz);ESI-MS m/z 280 [(M+H)+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloropyrazine-2-carboxylic acid, its application will become more common.

Reference:
Article; Inagaki, Yusuke; Ino, Katsutoshi; Ishizu, Kenichiro; Koike, Takanori; Maeda, Jun; Negoro, Kenji; Shimoshige, Yukinori; Takahashi, Taisuke; Tanaka, Hiroaki; Tsukamoto, Issei; Yokoyama, Kazuhiro; Bioorganic and medicinal chemistry; (2020);,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Application of 36070-80-1, A common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, molecular formula is C5H3ClN2O2, 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.

At 0 C., a solution of compound (4-2) (0.89 g. 5 mmol) in dichloromethane (20 mL) is added into a solution of 3-methoxy aniline (0.62 g, 5 mmol) and triethylamine (1.01 g, 10 mmol) in dichloromethane (100 mL) over 30 minutes, and the reaction mixture is heated to room temperature overnight. The reaction mixture is diluted with dichloromethane (100 mL), and the organic phase is washed with water and brine, dried through anhydrous sodium sulfate and filtered. After being evaporated, the residue is purified by silica gel column chromatography to give compound (4-3) (1.1 g, 80%),

The synthetic route of 36070-80-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HANGZHOU BENSHENG PHARACEUTICALS CO., LTD.; Xu, Rongzhen; Xie, Fuwen; Lai, Hongxi; Rong, Frank; US2013/178470; (2013); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem