Cyclopropylamine → HCID 67443346, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 139 (101 mg, 0.225 mmol) in THF (6 mL) at −35° C. was added TEA (0.094 mL, 1.126 mmol) and triphosgene (80 mg, 0.270 mmol) in THF (1 mL) and the mixture was warmed to −10° C. over an hr. Cyclopropylamine (64.3 mg, 1.126 mmol) was added and the reaction mixture was stirred at RT for 1.5 hrs. The reaction mixture was diluted with EtOAc then washed with saturated NH4Cl solution. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated. Purification by column chromatography (10% MeOH in EtOAc) afforded title compound 140 (20 mg, 17% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.69 (s, 1H), 8.53 (s, 1H), 8.50 (d, J=5.48 Hz, 1H), 8.32 (s, 1H), 8.22 (d, J=8.021, 1H), 7.81 (m, 1H), 7.70 (m, 1H), 7.36 (t, J=9.19 Hz, 1H), 7.18 (m, 1H), 6.62 (d, J=4.89 Hz, 1H), 6.55 (s, 1H), 4.62 (s, 2H), 2.68 (s, 4H), 2.53 (m, 1H), 0.63 (m, 2H), 0.41 (m, 2H). M (m/z)=532.543 (M+H)

Provenance & Evidence