Reaction #172299

Reaction equation

2-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid

thiazol-2-amine

HATU

DIEA

→

title compound 32

Yield 48.0%

tert-butyl 3-(2-(4-(thiazol-2-ylcarbamoyl)-1H-benzo[d]imidazol-2-yl)phenoxy)pyrrolidine-1-carboxylate

Yield 48.0%

Solvents

water

DMF

Conditions

Workup

1. 1
   workup.STIRRINGstirred for 30 min
2. 2
   FiltrationThe precipitate was collected by filtration
3. 3
   Otherpurified by column chromatography

Procedure

To a solution of 2-(2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yloxy)phenyl)-1H-benzo[d]imidazole-4-carboxylic acid (31; 150 mg, 0.36 mmol), thiazol-2-amine (4; 35.5 mg, 0.36 mmol), and HATU (202 mg, 0.53 mmol) in DMF (5 mL) was added DIEA (137 mg, 1.06 mmol). The mixture was stirred at room temperature for 18 h. It was then diluted with water (20 mL) and stirred for 30 min. The precipitate was collected by filtration, and then purified by column chromatography to give 85 mg of the title compound 32 (yield: 48%). MS (ESI) calcd for C26H27N5O4S: 505.18; found: 506 [M+H].

Source