Benzoic Acid → HCID 45275135, compound

Participants

Reaction Steps

To a solution of N-(2-aminoethyl)-1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide E13 (50 mg, 0.16 mmol), benzoic acid (23 mg, 0.19 mmol) and HATU (72 mg, 0.19 mmol) in DMF (1 mL) was added DIPEA (82 μL, 0.47 mmol). After 16 h the mixture was poured into a saturated solution of sodium hydrogen carbonate (50 mL) and extracted with EtOAc (2×25 mL). The combined organic extracts were washed with water (50 mL), a saturated solution of citric acid (50 mL) water (50 mL) and brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 9:1) to furnish the title compound as a white solid (24 mg, 36%), m.p. 209-211° C.; umax (CHCl3)/cm−1 3029, 3006, 1656, 1523, 1385, 1228, 1017; m/z (ESI) C20H22Cl2N4NaO2 requires 443.1012, found [M+Na]+ 443.1013.

Provenance & Evidence