1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69676479, compound

Participants

Reaction Steps

To a solution of N-(azepan-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (200 mg, 0.862 mmol) in DMF (4 mL) was added EDCI (196 mg, 1.03 mmol), HOBt (139 mg, 1.03 mmol), 2-(3,5-dichlorophenylamino)acetic acid (189 mg, 0.862 mmol) and DIEA (0.22 mL, 1.29 mmol) at 0° C. The reaction mixture was stirred overnight at rt, diluted with EtOAc (100 mL) and washed with water (50 mL). The organic layer was dried over Na2SO4 and evaporated in vacuo to give the crude compound that purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (150 mg, 40%). 1H NMR (DMSO-d6, 400 MHz): δ 13.49-13.36 (m, 1H), 8.27-7.96 (m, 2H), 6.74 (s, 1H), 6.67 (s, 1H), 6.62 (s, 1H), 6.34 (s, 1H), 4.50-4.30 (m, 1H), 4.08-3.8 (m, 5H), 3.36 (m, 2H), 1.8-2.2 (m, 2H), 1.8-1.35 (m, 2H), 1.3-1.1 (m, 2H), LCMS: m/z [M+1]=434 & [M+23]=456.

Provenance & Evidence