1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86706440, compound

Participants

Reaction Steps

To a cooled solution of 2-(3-chloro-5-fluorophenylamino)acetic acid (70 mg, 0.34 mmol) at 0° C. in DMF (5 mL), HOBt (69 mg, 0.51 mmol) was added and the reaction mixture was stirred for 10 min. before EDCI (101 mg 0.51 mmol), (R)—N-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (75 mg, 0.34 mmol) and DIEA (104 mg, 0.80 mmol) were added in succession. The reaction mixture was allowed to warm to rt and was stirred overnight. After completion of the reaction as indicated by TLC the reaction mixture was diluted with EtOAc (50 mL) and was washed with water (3×20 mL). The EtOAc layer was then dried over Na2SO4 and evaporated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (14 mg, 10%). 1H NMR (400 MHz, CD3OD): δ 8.52-8.43 (m, 1H), 6.45-6.08 (m, 4H), 4.49-3.82 (m, 5H), 3.31-2.95 (m, 2H), 1.96-1.63 (m, 4H). LC-MS: m/z [M+1]=404.

Provenance & Evidence