Category: 36070-80-1

Application of 36070-80-1, These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, 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 suspension of 5-chloropyrazine-2-carboxylic acid (365 mg, 2.302 mmol) in anhydrous DCM (6 mL) was added oxalyl dichloride (1.381 mL, 2.76 mmol), followed by a few drops of DMF. The reaction mixture was stirred at room temperature overnight. Solvent was evaporated, the residue was dissolved in anhydrous DCM (6 mL), 3-methoxyazetidine hydrochloride (341 mg, 2.76 mmol) was added, followed by DIEA (1.404 mL, 8.06 mmol). The reaction mixture was stirred at room temperature for 5 h. Solvent was evaporated, the residue was dissolved in ethyl acetate, washed with 5% citric acid solution, saturated NaHC03 aqueous solution, brine, and dried over anhydrous Na2S04. The mixture was filtered and concentrated. The residue was purified by column chromatography with 60% ethyl acetate/hexanes to give the title compound (269 mg, 1.18 mmol, 51 % yield) as an off-white solid. Exact mass calculated for CgHioClNsOz: 227.1 , found: LCMS mlz = 228.0 [M+H]+; lU NMR (400 MHz, CDC13) delta 3.33 (s, 3H), 4.09-4.13 (m, 1H), 4.25-4.30 (m, 1H), 4.37-4.42 (m, 1H), 4.48-4.54 (m, 1H), 4.79-4.84 (m, 1H), 8.53 (d, J = 1.3 Hz, 1H), 9.10 (d, J = 1.3 Hz, 1H).

Statistics shows that 5-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 36070-80-1.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; BUZARD, Daniel J.; LEHMANN, Juerg; NARAYANAN, Sanju; YUE, Dawei; WO2011/127051; (2011); 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, Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a cooled solution of 26 (3 g, 18.92 mmol, 1.0 eq), in N,N-dimethylformamide (30 mE) was added 1-[l3is (dimethylamino)methylene] -1 H-i ,2,3-triazolo[4,5-b]pyri- dinium 3-oxid hexafluorophosphate (8.65 g, 22.70 mmol, 1 .2 eq) and stirred at room temperature for 20 mm. Reaction mixture again cooled diisopropylethylamine (7.32 mE, 56.76 mmol, 3.0 eq) was added followed by addition of dimethylamine (0.851 g, 18.92 mmol, 1.0 eq). The reaction mixture was stirred at room temperature for 2 h. After completion of reaction, reaction mixture was transferred into water and product was extracted with ethyl acetate. Organic layer was combined, washed with brine solution, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was thrther purified by column chromatography and the compound was eluted in 0.9% methanol in dichioromethane to obtain 26.1(2.5 g, 71.18%). MS(ES): mlz 186.61 [M+H].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Nimbus Lakshmi, Inc.; Masse, Craig E.; Greenwood, Jeremy Robert; Mondal, Sayan; Cowen, Scott D.; McLean, Thomas H.; (624 pag.)US2019/31664; (2019); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route 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.

A solution of (R)-tert-butyl 2-methylpiperazine-l-carboxylate (0.5 g, 2.5 mmol), 5-chloropyrazine-2- carboxylic acid (0.4 g, 2.5 mmol), HATU (1.14 g, 3 mmol) and triethylamine (0.64 g, 6.4 mmol) in dichloromethane (5 ml) was stirred at room temperature for 2 hours. To the mixture was added water (30 mL) and the organics were extracted with dichloromethane (20 mL). The organic layer was dried over Na2S04 and concentrated to dryness, and the residue was purified by silica gel flash column chromatography, eluting with ethyl acetate: petroleum ether = 1:5 to afford the title compound (780 mg, 2.29 mmol, 92 % yield). LCMS Method D RT= 1.54 min, ES+ve 241 [M-Boc+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, 5-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CASILLAS, Linda N.; HARLING, John David; MIAH, Afjal Hussain; SMITH, Ian Edward David; RACKHAM, Mark David; (204 pag.)WO2017/182418; (2017); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, 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. 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid belongs to pyrazines compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 5-ch[oropyrazine-2-carboxy[ic acid [CAS RN: 36070-80-1] (1.00 g,6.31 mmo[, 1 .0 eq), tert-butyl. 4-aminopiperidine-1 -carboxylate [CAS-RN: 87120-72-7] (1.39 g, 6.94 mmo[, 1.1 eq), HATU (2.64 g, 6.94 mmo[, 1.1 eq) and DIPEA(2.33 mL, 12.6 mmo[, 2.0 eq) was dissolved in 38 mL DMF and stirred at rtovernight. The reaction mixture was partitioned between ethyl acetate andwater. The organic phase was washed with brine and filtered through a Whatman filter. The volatile components were removed in vacuo and the crude material obtained was purified via preparative MPLC (Biotage Isolera; 25 g SNAP cartridge: hexane-> hexane/ethyl acetate 2/3) to give 1 .01 g (43% yield oftheory) of the title compound.UPLC-MS (Method 2): R = 1.15 mm; MS (Elneg) m/z = 339 [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, 5-Chloropyrazine-2-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BAeRFACKER, Lars; SIEMEISTER, Gerhard; HEINRICH, Tobias; PRECHTL, Stefan; STOeCKIGT, Detlef; ROTTMANN, Antje; WO2015/113927; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference 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.

General procedure: The corresponding substituted salicylanilide 2 (1 mmol) and 5-chloropyrazine-2-carboxylic acid 1 (1 mmol) were dissolved in dryDMF (8 mL), the solution was cooled to 10 C and DCC (1.2 mmol)was added in three portions during 1 h. The mixture was stirred foradditional 3 h at the same temperature and then stored at 4 C for20 h. The precipitate of N,N0-dicyclohexylurea was removed byfiltration and the solvent was evaporated in vacuo till dryness. Thecrude products 3 were purified by one or repeated crystallizationfrom ethyl acetateehexane mixture.

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:
Article; Baranyai, Zsuzsa; Kratky, Martin; Vin?ova, Jarmila; Szabo, Nora; Senoner, Zsuzsanna; Horvati, Kata; Stola?ikova, Ji?ina; David, Sandor; Bosze, Szilvia; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 692 – 704;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Reference of 36070-80-1, These common heterocyclic compound, 36070-80-1, name is 5-Chloropyrazine-2-carboxylic acid, 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.

A solution of 5-chloropyrazine-2-carboxylic acid (200.0 g, 1.26 mol) in THF (2.5 L) was treated with a solution of tert-butyl 2,2,2-trichloroacetimidate (460 mL, 2.57 mol) in cyclohexane (2.5 L). The reaction was stirred at 25 C for 5 min and then treated with boron trifluoride dimethyl etherate (144.0 mL, 126 mmol). The resulting reaction mixture was stirred at 25 C for 16 h and then diluted with EtOAc (5.0 L), washed with a saturated aqueous sodium bicarbonate solution (4.0 L) followed by water (5.0 L). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (Silica 60-120 mesh, 10% EtOAc in hexanes) to give tert-butyl 5-chloropyrazine-2-carboxylate (250 g, 92%) as a colorless oil. MS (ESI, positive ion) m/z: 215.2 (M+1 )+. 1H NMR (400 MHz, CDCl3) delta 9.01 (d, J = 1.3 Hz, 1 H), 8.70 (d, J = 1.3 Hz, 1 H), 1.66 (s, 9H).

Statistics shows that 5-Chloropyrazine-2-carboxylic acid is playing an increasingly important role. we look forward to future research findings about 36070-80-1.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); 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., Recommanded Product: 5-Chloropyrazine-2-carboxylic acid

Step 1: 5-chloro-N-[(lS)-l-cyclopropyl-2,2,2-trifluoroethyl]pyrazine-2-carboxamide N,N-Diisopropylethylamine (1.3 mL, 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 (lS)-l- cyclopropyl-2,2,2-trifluoroethanamine hydrochloride (0.44 g, 2.5 mmol) (ASIBA Pharmatech, Cat.No.: 70092-HCl) in methylene chloride (10 mL). The reaction mixture was stirred at room temperature overnight. The mixture was worked up with saturated aqueous NaHC03, and extracted with ethyl acetate (3x 20 mL). The combined organic layers were washed with brine, dried over MgSC , 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 (0.51 g, 72%). LCMS (M+H) +: m/z = 280.0/282.0.

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; INCYTE CORPORATION; YAO, Wenqing; BURNS, David M.; ZHUO, Jincong; WO2012/177606; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Synthetic Route of 36070-80-1, 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. 36070-80-1 name is 5-Chloropyrazine-2-carboxylic acid, 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 RBF was charged with 3-pentyn-2-ol (2.06 mL, 22.08 mmol) and DMF (10 mL). Potassium t-butoxide, sublimed, 99.99% trace metals basis (1.24 g, 11.04 mmol) was added portionwise (cooling with water). The mixture was stirred at room temperature for 10 min until all t-BuOK went into solution, then 5-chloropyrazine-2-carboxylic acid (0.500 g, 3.15 mmol) was added in portions and the resulting brown suspension was heated at 75 C. for 45 minutes. The mixture was cooled to RT and diluted with water (20 ml) until all solids dissolved, then acidified with 2M HCl (5.5 ml) to pH 2. The resulting solution was extracted with EtOAc and the organic layer was washed with water and brine, filtered through a 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 (424 mg, 2.056 mmol, 65.2% yield) as a tan solid. m/z (ESI) 207.1 (M+H)+.

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; LEWIS, Richard T.; ALLEN, Jennifer R.; BROWN, James; GUZMAN-PEREZ, Angel; HUA, Zihao; JUDD, Ted; LIU, Qingyian; OLIVIERI, Philip R.; ROMERO, Karina; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; US2015/38497; (2015); 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.

The title compound is prepared by essentially following the procedure of Method C, using 5-chloro-pyrazine-2-carboxylic acid (Kiener, A.; Roduit, J.-P.; Tschech, A.; Tinschert, A.; Heinzmann, K. Synlett 1994, 814-16), (0.096 g, 1.20 mmol), oxalyl chloride (0.35 mL, 3.99 mmol) and N*2*-(2-dimethylamino-ethyl)-N*2*-methyl-benzothiazole-2,6-diamine (0.20 g, 0.80 mmol) to afford 0.21 g, (67%). MS (m/z): calcd for Ci7Hi9ClN6OS (M+H)+: 391.9; found: 391.2.

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; ELI LILLY AND COMPANY; WO2006/66173; (2006); A2;,
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 36070-80-1 as follows. Application In Synthesis of 5-Chloropyrazine-2-carboxylic acid

To a solution of 5-chloropyrazine-2-carboxylic acid (500 mg, 3.1 mmol) and methyl-6- aminohexanoate hydrochloride (688 mg, 3.71 mmol) in dichloromethane (15 mL) was added 1 -ethyl-3-(3-dimethylaminopropyl)carbodiimide (71 1 mg, 3.71 mmol, 1.2 equiv). The reaction was allowed to stir for 18 hours at room temperature and was then diluted with dichloromethane (75 mL) and washed with 1 N hydrochloric acid (15 mL). The layers were separated, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and the residue was purified by flash column chromatography over silica gel (gradient elution with 20%-70% ethyl acetate in heptane) to provide methyl 6-{[(5-chloropyrazin-2-yl)carbonyl]- amino}hexanoate, 20 (378 mg, 43%), as a white solid. LCMS (Protocol E): m/z 308.2

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; PFIZER INC.; DUSHIN, Russell George; ABRAMITE, Joseph A.; CASAVANT, Jeffrey M.; CHE, Ye; FILZEN, Gary Frederick; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; MOINE, Ludivine; O’DONNELL, Christopher John; ROBERTS, Lee; STARR, Jeremy; TUMEY, Lawrence N.; UCCELLO, Daniel P.; YOUNG, Jennifer; (135 pag.)WO2018/25168; (2018); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem