2-(Dimethylamino)ethanol → HCID 70961728, compound

Participants

Reaction Steps

A solution of (1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethylcarbamate (31-1, 50 mg, 0.096 mmol) in 2-(dimethylamino)ethanol (1 mL) was heated at 100° C. for 1 hour. The reaction mixture was cooled, then partitioned between ethyl acetate (40 mL) and brine (3×40 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (EtOAc initially, grading to 10% saturated NH3/ethanol in EtOAc) to give 2-(dimethylamino)ethyl(1S)-1-cyclopropyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethylcarbamate (31-2) as a pale yellow solid. 1H NMR (500 MHz, CDCl3) showed a 2:1 mixture of rotamers; major rotamer: δ 7.42-7.24 (m, 5H), 7.11-6.95 (m, 3H), 6.41 (br s, 1H), 5.93 (m, 1H), 5.58 (d, 1H, J=7.6 Hz), 5.04 (br d, 1H, J=13.9 Hz), 4.91 (ddd, 1H, J=14.7, 4.4, 1.7 Hz), 4.30 (t, 1H, J=7.8 Hz), 4.15 (m, 2H), 2.54 (m, 2H), 2.27 (s, 6H), 1.14 (m, 1H), 0.57-0.33 (m, 4H). LRMS nil/z (M+H) 470.5 found, 470.2 required.

Provenance & Evidence