Cyclopropylamine → 2-(5-Bromo-2-chloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid cyclopropylamide

Diisopropylethylamine (1.19 mL, 6.82 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.650 g, 3.41 mmol) and 1-hydroxybenzotriazole (0.460 g, 3.41 mmol) are sequentially added to a stirred suspension of 2-(5-bromo-2-chloropyrimidin-4-yl)-benzo[b]thiophene-4-carboxylic acid (1.20 g, 3.25 mmol) in anhydrous dichloromethane (25 mL) at ambient temperature under nitrogen. The resultant light suspension is treated with cyclopropylamine (0.190 g, 3.41 mmol), then the reaction mixture is allowed to stir for 5 hours. The reaction mixture is diluted with dichloromethane (50 mL) before it is washed with water (100 mL). The aqueous layer is extracted with dichloromethane (100 mL×2) to ensure no precipitation is present in the aqueous layer. The combined organic layers are concentrated and then resuspended in dichloromethane (1 mL)/diethyl ether (9 mL). After sonication and subsequent filtration, the solid is washed with additional dichloromethane (1 mL)/diethyl ether (9 mL) and dried to provide the title compound (1.10 g, 97% yield).

1. washis washed with water (100 mL)
2. extractionThe aqueous layer is extracted with dichloromethane (100 mL×2)
3. customno precipitation
4. concentrationThe combined organic layers are concentrated
5. customAfter sonication and subsequent filtration
6. washthe solid is washed with additional dichloromethane (1 mL)/diethyl ether (9 mL)
7. customdried

ORD record

ord-a93ca9c9a8be42fda77f92c5dc9361d0

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547691B2