Cyclopropylamine → HCID 67048300, compound

Participants

Reaction Conditions

Reaction Steps

The solution of aniline 359 (136 mg, 0.312 mmol) and DIPEA (0.218 mL, 1.246 mmol) in THF (6 mL) was cooled to 0° C., and then triphosgene (46.2 mg, 0.156 mmol) was added and the reaction mixture was stirred for 1 h at 0° C. followed by an addition of cyclopropylamine (89 mg, 1.558 mmol). The reaction mixture was stirred at r.t. for an additional 3 hrs then concentrated, partitioned between water and ethyl acetate. A thick solid was formed which was isolated by suction filtration, rinsed with water and ethyl acetate, and dried in vacuo. This material was then purified using Gilson (eluent 20-95% MeOH/H2O, 1 h) to give the title compound 360 (30 mg, 0.058 mmol, 18.53% yield) as a white solid. 1HNMR (DMSO-d6) d(ppm) 1H:HNMR 9.16 (s, br, 1H), 8.16 (d, 1H, J=1.6 HZ), 8.11 (d, 1H, J=5.4 Hz), 7.91 (s, 1H), 7.83 (d, 1H, J=8.2 Hz), 7.46 (dd, 1H, J1=2.1 Hz, J2=8.2 Hz), 7.34 (dd, 1H, J1=2.6 Hz, J2=13.9 Hz), 6.97-7.45 (m, 2H), 6.84-6.81 (m, 1H), 6.23 (d, 1H, J=4.7 Hz), 3.18 (t, 4H), 3.14 (s, 2H), 2.15-2.12 (m, 1H), 1.98 (m, 4H), 0.23-0.19 (m, 2H), 0.02-0.005 (m, 2H). MS: 520.4 (MH)+.

Provenance & Evidence