4-Methylmorpholine → HCID 67444559, compound

Participants

Reaction Steps

To a suspension of 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.158 g, 0.477 mmol; Example 58D) in dichloromethane (2 mL) was added a catalytic amount of N,N-dimethylformamide followed by oxalyl dichloride (2.0 Min dichloromethane) (0.358 mL, 0.715 mmol). After stirring for 30 minutes, the reaction was concentrated. The residue was dissolved in dichloromethane (2 mL) and 5-(trifluoromethyl)pyridin-2-amine (0.066 g, 0.405 mmol) and N-methylmorpholine (0.079 mL, 0.715 mmol) were added. After stirring for 2 hours, the reaction was loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes (Flow=30 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 8.55 (d, J=12.2, 1H), 8.25 (d, J=8.8, 1H), 7.92 (dd, J=2.2, 8.8, 1H), 7.33 (ddd, J=2.7, 5.3, 7.1, 4H), 7.06-6.96 (m, 4H), 4.22 (s, 2H), 3.55 (t, J=6.5, 2H), 2.83 (t, J=6.5, 2H); MS (ESI+) m/z 467.1 (M+H)+.

Provenance & Evidence