Dimethylformamide → HCID 86623844, compound

Participants

Reaction Steps

General Procedure for the synthesis of amides 26 from acid 30a: TBTU (48 mg, 0.15 mmol) is added to a solution of acid 30a (41 mg, 0.12 mmol) in DMF (1.5 mL), cooled by ice/water. After 30 min, amine 29 or its hydrochloride salt (0.14 mmol) and triethylamine (22 μL, 0.16 mmol if free amine is used, twice the amount if the hydrochloride salt is used) are added, the cooling bath is removed, and the reaction mixture is stirred at ambient temperature until TLC indicates complete consumption of the acid. DMF is then evaporated, the residue is partitioned between EtOAc (15 mL) and water (10 mL), and the aqueous layer is extracted with more EtOAc (3×15 mL). The combined organic layers are washed with 2N NaOH, water (2×) and brine, dried over MgSO4, filtered and concentrated. The crude material is purified by chromatography followed by trituration or crystallization.

Provenance & Evidence