Cyclopropylamine → HCID 67443029, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of aniline 216 (130 mg, 0.262 mmol) in THF (10 mL) at 0° C. was added DIPEA (0.137 mL, 0.785 mmol) and triphosgene (38.8 mg, 0.131 mmol). The reaction mixture was stirred at 0° C. for 1 hr before cyclopropylamine (0.054 mL, 0.785 mmol) was added and the mixture was stirred for 10 min at 0° C. The reaction mixture was slowly warmed to room temperature and stirred over weekend then partitioned between NaHCO3 saturated solution and EtOAc. The organic layer (suspension) was concentrated, the residue was dry-loaded onto a column (Biotage, MeOH/DCM, 0-25%, SNAP 10 g cartridge), purified twice then triturated with ether and acetone to give title compound 217 (30.4 mg, 0.052 mmol, 20% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.75 (s, 1H), 8.59 (d, 1H, J=5.5 Hz), 8.48 (m, 1H), 8.07 (s, 1H), 7.78-7.74 (m, 1H), 7.71 (s, 1H), 7.42 (t, 1H, J=9.0 Hz), 7.25-7.22 (m, 1H), 6.74 (d, 1H, J=5.5 Hz), 6.61-6.60 (m, 1H), 4.22 (s, 3H), 3.62 (t, 4H, J=4.5 Hz), inside 3.38-3.33 (m, 2H), 2.60-2.57 (m, 1H), 2.52-2.46 (m, 6H), 0.71-0.67 (m, 2H), 0.48-0.46 (m, 2H). MS: 580.6 (MH)+

Provenance & Evidence