1-Hydroxybenzotriazole → HCID 53476794, compound

Participants

Reaction Steps

A mixture of 3-(1,4′-bipiperidin-1′-ylmethyl)-7-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (0.100 g, 0.174 mmol), (1S)-1-phenylethanamine (0.032 g, 0.261 mmol), EDC (0.167 g, 0.869 mmol), HOBT (0.027 g, 0.174 mmol), and N,N-diisopropylethylamine (0.303 mL, 1.74 mmol) in N,N-dimethylformamide (2 mL) and 1,2-dichloroethane (2 mL) was stirred at room temperature overnight before it was heated to 50° C. for 4 h. The solvent was removed under reduced pressure. The residue was dissolved in DMSO and purified via HPLC (Waters, 30-80% MeCN/H2O with 0.1% TFA). The fractions containing the product were neutralized with saturated aqueous NaHCO3, acetonitrile was removed under reduced pressure, and the residue was diluted with water. The solid material was collected by filtration, washed with water, and air dried to afford 3-(1,4′-bipiperidin-1′-ylmethyl)-7-(methylsulfonyl)-N-[(1S)-1-phenylethyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxamide (0.086 g, 73% yield). MS (m/z) 679.3 (M+H+).

Provenance & Evidence