1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68070462, compound

Participants

Reaction Steps

To a solution of N-(azepan-3-yl)-N-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (350 mg, 1.4 mmol) in DMF (7 mL) was added EDCI (409 mg, 2.1 mmol), HOBt (287 mg, 2.1 mmol), 2-(3,5-dichlorophenylamino)acetic acid (312 mg, 1.4 mmol) and DIEA (0.5 mL, 2.8 mmol) at 0° C. The reaction mixture was stirred at rt overnight and diluted with water and ethyl acetate (3:1, 400 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 (325 mg 51%) the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 13.50 and 13.44 (2s, 1H), 8.25-8.19 (m, 2H), 6.74 (s, 1H), 6.68 (s, 1H), 6.62 (s, 1H), 6.36 (bs, 1H), 4.21-3.71 (m, 5H), 3.42-3.01 (m, 2H), 3.31 (s, 3H), 1.93-1.65 (m, 6H). LC-MS: m/z [M+1]=448.

Provenance & Evidence