Acetone → HCID 67441539, compound

Participants

Reaction Steps

To a solution of 126 (150 mg, 0.346 mmol) in THF (6 mL) was added TEA (175 mg, 1.730 mmol) and triphosgene (103 mg, 0.346 mmol) in THF (1 mL) and the mixture was stirred for 30 minutes. 3-(Methylsulfonyl)benzenaminium chloride (144 mg, 0.692 mmol) was added and the mixture was stirred at RT overnight. The mixture was then concentrated and the resultant solid was triturated with acetone, DCM and MeOH, followed by recrystallization from hot DMF. An additional trituration with acetone afforded 130 (25 mg, 11% yield) as a grey powder. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.32 (s, 1H), 9.24 (s, 1H), 8.52 (d, J=5.48 Hz, 1H), 8.16 (s, 1H), 8.13 (s, 1H), 7.94 (d, J=8.41 Hz, 2H), 7.75 (m, 1H), 7.66-7.62 (m, 3H), 7.56-7.53 (m, 2H), 7.45 (m, 1H), 7.31 (m, 1H), 6.64 (d, J=5.48 Hz, 1H), 3.48-3.37 (m, 4H), 3.19 (s, 3H), 1.86-1.81 (m, 4H). MS (m/z)=631.437 (M+H).

Provenance & Evidence