Triethylamine → HCID 86706462, compound

Participants

Reaction Steps

To a cooled solution of 2-(3-chloro-5-fluorophenylamino)acetic acid (139 mg, 0.68 mmol) at 0° C. in DMF (5 mL) was added HOBt (136 mg, 0.10 mmol), EDCI (197 mg, 0.10 mmol), (S)-4-(piperidin-3-yloxy)-7H-pyrrolo[2,3-d]pyrimidine hydrochloride (150 mg, 0.7 mmol) and Et3N (0.2 mL, 1.37 mmol) at 0° C. The reaction mixture was allowed to warm to rt and was stirred overnight. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (3×20 mL). The combined EtOAc layer was dried over Na2SO4 and concentrated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford (45 mg, 17%) the titled compound. 1H NMR (400 MHz, DMSO-d6): δ 12.08 and 12.05 (2s, 1H), 8.41 and 8.39 (2s, 1H), 7.35 (s, 1H), 6.62-6.25 (m, 4H), 5.39-5.24 (m, 1H), 4.05-3.62 (m, 5H), 3.55-3.42 (m, 2H), 1.89-1.45 (m, 4H). LC-MS: m/z [M+1]=404.

Provenance & Evidence