Реакция #92432

Уравнение реакции

N-(5-(5-(2-bromoacetyl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide

thiourea

→

crude residue

Выход 14.7%

N-(5-(5-(2-aminothiazol-5-yl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide

Выход 14.7%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was quenched
2. 2
   Экстракцияextracted as in Example 1(d)
3. 3
   workup.DISTILLATIONThe solvent was distilled off

Методика

To a solution of N-(5-(5-(2-bromoacetyl)-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)acetamide (100 mg, 0.20 mmol) in ethanol was added thiourea (20 mg, 0.30 mmol, 1.5 eq). The mixture was stirred at 60° C. for 3 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off to give the crude residue which was purified by preparative HPLC to give the product in 14.7% yield (14 mg). 1H NMR (300 MHz, CD3OD): δ 8.73 (s, 1H), 8.11 (s, 1H), 8.01 (s, 1H), 7.73-7.69 (m, 2H), 7.62-7.50 (m, 2H), 7.45 (d, 1H), 7.10-6.99 (m, 3H), 2.10 (s, 3H); LC-MS (ESI): Calculated mass: 461.4; Observed mass: 462.1 [M+H]+ (rt: 0.80 min).

Источник