1-Hydroxybenzotriazole → HCID 57874365, compound

Participants

Reaction Steps

DIPEA (135 mg, 11.0 mmol) was added to a stirred solution of N-biphenyl-4-yl-malonamic acid (64 mg, 0.3 mmol) in DMF (2.0 mL) followed by HOBt (61 mg, 0.45 mmol) and EDCI.HCl (85 mg, 0.45 mmol). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (60 mg, 0.3 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethylacetate, washed with brine and concentrated The residue was purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3) to afford 27 mg (19.7% Yield) of N-biphenyl-4-yl-3-[4-(3-cyano-phenoxy)-piperidin-1-yl]-3-oxo-propionamide. LC/MS [M+H]+: 440.2, 98.14%, 1H NMR (300 MHz, DMSO-d6): δ10.2 (s, 1H), 7.7 (m, 5H), 7.5 (m, 5H), 7.3 (m, 2H), 4.8 (m, 1H), 4.0 (m, 1H), 3.8 (m, 1H), 3.6 (m, 2H), 3.3 (m, 2H), 2.0 (m, 2H), 1.7 (m, 1H), 1.6 (m, 1H).

Provenance & Evidence