Dimethylformamide → HCID 46209239, compound

Participants

Reaction Steps

To a solution of intermediate B-15 (170 mg, 0.6 mmol) and intermediate A-10 (185 mg, 0.67 mmol) in DMF (8 mL) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (173 mg, 0.9 mmol, EDCI), 1-hydroxybenzotriazole (122 mg, 0.9 mmol, HOBT), and N,N-diisopropylethylamine (200 μL, 1.2 mmol). The reaction mixture was stirred at RT for 17 h. The mixture was poured into water (150 mL). The precipitate was filtered, dissolved in DMF and purified by chromatography on a C-18 reverse phase column (eluant: acetonitrile/water gradient) to give 2-(3-methyl-1-piperidinyl)-N-[6-[3-oxo-4-(phenylmethyl)-1-piperazinyl]-3-pyridinyl]-4-(trifluoromethyl)-5-oxazolecarboxamide (31) (169 mg, 52% yield) 1H NMR (500 MHz, CDCl3) δ 8.28 (s, 1H), 8.04 (d, 1H, J=9 Hz), 7.61 (s, 1H), 7.4-7.3 (m, 5H), 6.64 (d, 1H, J=9 Hz), 4.73 (s, 2H), 4.23 (s, 2H), 4.15 (bt, 2H), 3.88 (t, 2H, J=5.5 Hz), 3.43 (t, 2H, J=5.5 Hz), 3.08 (dt, 1H), 2.75 (t, 1H, J=12 Hz), 1.97-1.74 (m, 3H), 1.31 (bs, 1H), 1.28-1.16 (m, 2H), 1.03 (d, 3H, J=6.5 Hz). LCMS (ESI) Rt=3.83 min, 543.3 [M+1]+.

Provenance & Evidence