N-(3-amino-4-bromophenyl)-3-(2-cyanopropan-2-yl)benzamide → N-(2-bromo-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide

HRID 1184874Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:20]#[N:21])([CH3:19])[CH3:18])[CH:12]=2)[CH:5]=[CH:6][C:7]=1[Br:8].[N:23]1[CH:28]=[CH:27][N:26]=[C:25]2[S:29][C:30]([C:32](Cl)=[O:33])=[CH:31][C:24]=12>O1CCOCC1.O>[Br:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([C:20]#[N:21])([CH3:18])[CH3:19])[CH:12]=2)=[CH:3][C:2]=1[NH:1][C:32]([C:30]1[S:29][C:25]2=[N:26][CH:27]=[CH:28][N:23]=[C:24]2[CH:31]=1)=[O:33]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(3-amino-4-bromophenyl)-3-(2-cyanopropan-2-yl) 62 (215 mg, 0.600 mmol) and thieno[2,3-b]pyrazine-6-carbonyl chloride 63 (238 mg, 1.2 mmol) in dioxane (1 mL) was stirred for 2 h in microwave at 100° C. The reaction mixture was poured out in water, precipitate filtered off and washed with water and dried. Crystallization with acetonitrile gave crude compound 64 (340 mg, 109%). A sample of compound 64 was purified by HPLC to give the title compound N-(2-bromo-5-(3-(2-cyanopropan-2-yl)benzamido)phenyl)thieno[2,3-b]pyrazine-6-carboxamide 64. NMR (400 MHz, DMSO-d6) 1.76 (s, 6H), 7.62 (t, d=7.8 Hz, 1H), 7.72-7.80 (m, 3H), 7.96 (d, J=7.8 Hz, 1H), 8.06 (m, 2H), 8.57 (s, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.90 (d, J=2.3 Hz, 1H), 10.55 (s, 1H), 10.76 (s, 1H).

Workup

filtrationprecipitate filtered off
washwashed with water
customdried
customCrystallization with acetonitrile
customgave crude compound 64 (340 mg, 109%)
customA sample of compound 64 was purified by HPLC

Sources & evidence

ORD record: ord-d4105e96d68148f1aa0cd9f8da2d0903
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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