Dichloromethane → HCID 11301851, compound

Participants

Reaction Steps

6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt (0.272 mmol, 100 mg) is suspended in 5 mL of 1:1 DMF:DCM. DIEA is added dropwise until pH=9 by pH paper. Methyl isothiocyanate (0.299 mmol, 0.022 g) is added and the reaction is stirred at ambient temperature for 3 hrs. The reaction mixture is concentrated in vacuo and the crude material is purified by reversed-phase HPLC to afford the title compound (66.1 mg, 78.7%). 1H NMR (DMSO-d6, 300 MHz) δ 7.85 (1H, d, J=2.5 Hz), 7.71 (1H, dd, J=2.75, 9 Hz), 7.55 (1H, br m), 7.46 (1H, d, J=9 Hz), 5.95 (1H, s), 4.24 (2H, t, J=5.75 Hz), 3.59 (2H, br s), 2.79 (3H, br s), 2.07 (2H, m); MS (ESI, Pos.) calcd for C14H15ClN2O3S m/z [M+H]=327.0, found 327.0.

Provenance & Evidence