Formaldehyde → HCID 71730896, compound

Participants

Reaction Steps

To a suspension of 3-(4-chlorobenzo[d]thiazol-2-yl)-7-(piperazin-1-yl)-2H-pyrano[2,3-b]pyridin-2-one hydrochloride (890 mg, 2.0 mmol) m DMF (10 mL) were added 37% aqueous HCHO (0.4 mL, 3.4 mmol) and then NaBH(OAc)3 (636 mg, 3.0 mmol). The reaction mixture was stirred for 30 min at ambient temperature. To the mixture were added water (10 mL) and a saturated NaHCO3 solution (10 mL) to form a precipitate. The precipitate was filtered off, washed with water and dried under nitrogen, affording 680 mg (97%) of the title compound as a yellow solid. Melting point 258-260° C.; MS m/z 413.2 [M+H]+; 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.06 (1H, s), 8.25 (1H, d, J=8.8 Hz), 8.14 (1H, d, J=6.9 Hz), 7.64 (1H, m), 7.44 (1H, d, J=7.7 Hz), 7.08 (1H, d, J=9.1 Hz), 3.79 (4H, m), 2.44 (4H, m), 2.25 (3H, s).

Provenance & Evidence