Category: Pyrazines

1458-16-8, 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. 1458-16-8 name is Methyl 3-amino-6-iodopyrazine-2-carboxylate, 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.

Example 3b: 3-amino-6-iodopyrazine-2-carboxamide 30 ml of ammonia in water is added under magnetic stirring to 15 g (53.8 mmol) of a solution of methyl 3-amino-6-iodopyrazine-2-carboxylate in 150 ml of methanol. The reaction medium is stirred at 25C for 48 hours. After evaporation of the solvents, the precipitate obtained is filtered, rinsed with water and then dried at 50C to yield 12.50 g of 3-amino-6-iodopyrazine-2-carboxamide (88%) in the form of a beige solid. LCMS (EI, m/z): (M+l) 265.02 1H NMR: deltaEta ppm (400 MHz, DMSO): 8.35 (1H, s, CHarom), 7.85 (1H, bs, NH), 7.60 (3H, bs, NH), 3.25 (3H, s, CH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-6-iodopyrazine-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; PIERRE FABRE MEDICAMENT; KRUCZYNSKI, Anna; CREANCIER, Laurent; KALOUN, El Bachir; BEDJEGUELAL, Karim; RABOT, Remi; WO2014/16434; (2014); 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. 6863-74-7, name is 6-Chloropyrazine-2-carbonitrile belongs to Pyrazines compound, it is a common compound, a new synthetic route is introduced below. 6863-74-7

A mixture of tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol), 6- chloropyrazine-2-carbonitrile (3.34 mg, 0.024 mmol), cesium carbonate (15.62 mg, 0.048 mmol), BINAP (0.746 mg, 1.199 mmol) and Pd2(dba)3 (1.098 mg, 1.199 mmol) in degassed dioxane (1.0 mL) under nitrogen in a seal vial was stirred at 90C for 18 hour. The mixture was diluted with EtOAc (5 mL) and was washed with a solution of aqueous saturated sodium bicarbonate (5 mL). The organic layer was dried over sodium sulfate and concentrated to give crude tert-butyl ((1R,4R,7R)-2-(1-(azetidin-3-ylmethyl)-2-(1- (cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1H-benzo[d]imidazole- 5-carbonyl)-2-azabicyclo[2.2.1]heptan-7-yl)carbamate (15 mg, 0.024 mmol). Material was used as is in next reaction.

The synthetic route of 6863-74-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NGU, Khehyong; (435 pag.)WO2020/33514; (2020); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Some common heterocyclic compound, 5521-55-1, name is 5-Methylpyrazine-2-carboxylic acid, molecular formula is C6H6N2O2, 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. 5521-55-1

A solution of compound 20-12 (0.2 g, 0.2 mmol) in isopropanol (2 mL) was cooled to 0 C, and a solution of HC1 in isopropanol (40%, 5 mL) was added. The mixture was stirred until no more gas evolution. The mixture was filtered to afford a white solid; the solid was washed with EtOAc (5 mL). A round-bottom flask was charged with the white solid, compound 22-1 (0.1 g, 0.7 mmol), EDCI (0.2 g, 1.5 mmol) and HOAT (0.15 g, 1.1 mmol), and then DCM (10 mL) was added under N2. The mixture was cooled to 0 C, and DIPEA (0.5 mL, 3 mmol) was added slowly. The mixture was stirred at 30 C for 6 hours. After the reaction was complete, the mixture was quenched with water (10 mL). The resulting mixture was extracted with DCM (10 mL) twice. The combined organic layers were washed with saturated aqueous NaC1 (10 mL), dried over anhydrous Na2SO4, and then concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V:V) = 2:1 to give compound 20-2 (0.163 g, 70%) as a white solid.MS (ESI, pos.ion) m/z: 900.4[M+1] and ?HNMR (600 MHz, CDC13): (510.25 (s, 1H), 9.07 (s, 1H), 8.43 (s, 1H), 8.17 (d, J= 6.8 Hz,1H), 7.86-7.78 (m, 2H), 7.48 (s, 1H), 7.05 (s, 1H), 6.95 (d, J 9.1 Hz, 1H), 5.74 (dd, J 18.0,8.6 Hz, 1H), 5.51 (s, 1H), 5.02 (t, J= 9.5 Hz, 1H), 4.72-4.65 (m, 2H), 4.51 (d, J= 11.4 Hz, 1H),4.14-4.11 (m, 1H), 3.78 (s, 3H), 3.26-3.19 (m, 2H), 2.74-2.69 (m, 1H), 2.67-2.55 (m, 9H),2.29 (dd, J= 17.3, 8.6 Hz, 1H), 2.07 -2.00 (m, 2H), 1.95 – 1.89 (m, 2H), 1.78 (t, J= 10.0 Hz,1H), 1.64 (dd, J= 9.2, 5.9 Hz, 1H), 1.50 (s, 3H), 1.41 (d, J= 6.9 Hz, 7H), 1.27 (d, J= 3.5 Hz,2H), 1.20 (s, 3H), 0.92- 0.75 (m, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5521-55-1, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; LUO, Huichao; REN, Qingyun; XIONG, Zhimin; LIU, Yang; LEI, Yibo; XIONG, Jinfeng; ZHANG, Jiancun; (123 pag.)WO2016/127859; (2016); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem