Cyclopropylamine → HCID 67443701, compound

Participants

Reaction Steps

To a solution of 122 (65 mg, 0.144 mmol) in THF (7 mL) was added TEA (0.06 mL, 0.433 mmol) and triphosgene (42.8 mg, 0.144 mmol) in THF (2 mL) and the mixture was stirred at RT for an hour. Cyclopropylamine (16.48 mg, 0.289 mmol) was added and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM and washed with saturated NH4Cl solution. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. The resultant solid was triturated with acetone to afford title compound 123 (18 mg, 23% yield) as an olive colored solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.55 (s, 1H), 8.51 (d, J=5.48 Hz, 1H), 8.34 (s, 1H), 8.25 (d, J=8.22 Hz, 1H), 7.82 (m, 1H), 7.71 (m, 1H), 7.36 (t, J=8.99 Hz, 1H), 7.19 (m, 1H), 6.63 (d, J=5.48 Hz, 1H), 6.55 (s, 1H), 4.60 (s, 2H), 4.12 (s, 2H), 3.83 (m, 2H), 3.36 (m, 2H), 2.49 (m, 1H), 0.64 (m, 2H), 0.42 (m, 2H). MS (m/z)=534.51 (M+H)

Provenance & Evidence