Diisopropylethylamine → HCID 178512992, compound

Participants

Reaction Steps

6-Chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt (200 mg, 0.543 mmol) is suspended in 7 mL of DCM. Diisopropylethylamine is added dropwise until pH=9 by pH paper. N,N′-Bis(tert-butoxycarbonyl)-1-H-pyrazole-1-carboxamidine (169 mg, 0.543 mmol) is added and is stirred at ambient temperature overnight. The reaction mixture is concentrated in vacuo and Et2O is added to form a white precipitate, which is filtered and is washed with Et2O. The crude material is treated with neat TFA (10 mL) for 30 min at ambient temperature. The TFA is removed under reduced pressure. Et2O is added to precipitate the product, which is filtered, is washed with Et2O, and is dried. The crude material is further purified by reversed-phase HPLC to afford the title compound as the trifluoroacetic acid salt. (108 mg, 48.6%). %). 1H NMR (DMSO-d6, 300 MHz) δ 7.86 (1H, d, J=2.5 Hz), 7.72 (1H, dd, J=2.5, 8.75 Hz), 7.64 (1H, t, J=5.5 Hz), 7.47 (1H, d, J=8.75 Hz), 7.12 (3H, br s), 6.00 (1H, s), 4.26 (2H, t, J=5.75 Hz), 3.36 (2H, m, J=6.25 Hz), 2.04 (2H, m, J=6.25 Hz); MS (ESI, Pos.) calcd for C13H14ClN3O3 m/z [M+H]=296.1, found 296.0.

Provenance & Evidence