Category: 63744-29-6

Application of 63744-29-6, A common heterocyclic compound, 63744-29-6, name is 5-Bromo-[1,2,4]triazolo[4,3-a]pyrazine, molecular formula is C5H3BrN4, 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 1.30. (3 ?,4S)-4-methylbenzyl 4-(([l,2,4]triazolo[4,3-a]pyrazin-5-ylamino)methyl)-3-fluoro- piperidine-l-carboxylate (E2-2.2). [0269] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (160 mg, 0.80 mmol), (3R,4S)-4- methylbenzyl 4-(aminomethyl)-3-fluoropiperidine-l-carboxylate hydrochloride (306 mg, 0.96 mmol), Brettphos precatalyst (20 mg), Brettphos (20 mg), and Cs2C03 (789 mg, 2.4 mmol) in t-BuOH (6 mL) was heated to 100C in the sealed tube under N2 atmosphere. After stirring overnight at 100C, the mixture was cooled down to room temperature and concentrated under vacuum. The concentrate was partitioned into DCM and water. The aqueous phase was extracted with DCM. The combined organic phases were washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (eluent: 100% ethyl acetate) to afford the title compound as a brown powder (92 mg, 28%). MS (ESI) calcd for C2oH23FN602: 398.2; found: 399.3[M+H]. *H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.41 (d, J = 4.4 Hz, 1H), 7.34 (d, J = 4.4 Hz, 1H), 7.25 (d, J = 7.2 Hz, 2H), 7.17 (d, J = 7.2 Hz, 2H), 6.58 (br s, 1H), 5.09 (br s, 2H), 4.90-4.69 (m, 1H), 4.65-4.15 (m, 2H), 3.75-3.60 (m, 2H), 3.02-2.70 (m, 2H), 2.35 (s, 3H), 2.24-2.08 (m, 1H), 1.75- 1.65 (m, 2H).

The synthetic route of 63744-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem

Electric Literature of 63744-29-6, The chemical industry reduces the impact on the environment during synthesis 63744-29-6, name is 5-Bromo-[1,2,4]triazolo[4,3-a]pyrazine, I believe this compound will play a more active role in future production and life.

Step 1: (3S,4 ?)-tert-butyl 4-(([l,2,4]triazolo[4 -a]pyrazin-5-ylamino)methyl)-3-fluoropiperidine- 1-carboxylate [0185] A mixture of 5-bromo-[l,2,4]triazolo[4,3-a]pyrazine (102 mg, 0.51 mmol), (3S,4R)-tert-butyl 4- (aminomethyl)-3-fluoropiperidine-l-carboxylate (80 mg , 0.34 mmol) and DIPEA (1.2 mL, 1.0 mmol) in ethylene glycol (2 mL) was heated to 110 C in the sealed tube for 7 hr under N2 atmosphere. The mixture was allowed to cool to rt and concentrated. The concentrate was partitioned into DCM and water. The organic phase was washed with water, brine, dried over Na2S04 and concentrated. The concentrate was purified by column chromatography over silica gel (MeOH/DCM=50/l) to afford the title compound as an off-white powder (60 mg, 50%). MS (ESI) calcd for C16H23FN602: 350.2; found: 351.3[M+H]. 1H NMR (400 MHz, CDCI3) delta 8.72 (s, 1H), 7.41 (d, J = 4.8 Hz, 1H), 7.34 (d, J = 4.8 Hz, 1H), 6.55-6.47 (m, 1H), 4.90-4.65 (m, 1H), 4.62-4.35 (m, 1H), 4.33-4.05 (m , 1H), 3.74-3.64 (m, 2H), 2.96-2.62 (m, 2H), 2.24 -2.04 (m, 1H), 1.73-1.58 (m, 1H), 1.46 (s, 9H).

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-Bromo-[1,2,4]triazolo[4,3-a]pyrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (239 pag.)WO2016/100349; (2016); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem