Hydrochloric Acid → HCID 44194488, compound

Participants

Reaction Conditions

Reaction Steps

Concentrated hydrochloric acid (1 mL) was added to a stirred solution of 6-chloro-N-(1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)ethyl)-2H-chromene-3-carboxamide (178 mg, 0.4 mmol) in methanol (5 mL, 0.1 mol) at room temperature. The mixture was heated to 50° C. and stirred for 1 hour. TLC indicated complete reaction, so after allowing to cool, the mixture was concentrated under vacuum and the residue partitioned between sat'd NaHCO3 (30 mL—care: initial evolution of gas as reaction with excess acid ensues) and EtOAc (50 mL). The organic layer was washed with brine (1×20 mL), dried (MgSO4), filtered and the solvent removed under vacuum to leave a crude solid. The solid was triturated with EtOAc (10 mL) and filtered. The filter cake was washed with EtOAc (2×3 mL) to give the product (35 mg). m/z=354.3 (M+1)+. 1H NMR (400 MHz; DMSO-d6) δ 13.00 (s, 1H), 8.64 (d, J=8.0 Hz, 1H), 8.04 (s, 1H), 7.70 (s, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.39 (m, 1H), 7.32-7.24 (m, 3H), 6.86 (d, J=8.4 Hz, 1H), 5.21-5.13 (m, 1H), 4.97-4.88 (m, 2H), 1.48 (d, J=7.0 Hz, 3H).

Provenance & Evidence