Sodium hydride → HCID 8781137, compound

Participants

Reaction Steps

Added sodium hydride (73 mg; 2.89 mmol) to a stirred suspension of 21 (90 mg; 0.27 mmol) in dry tetrahydrofuran under nitrogen at room temperature. After 30 minutes, isonicotinoyl chloride hydrochloride (150 mg; 0.84 mmol) was added and the mixture allowed to stir for 72 hr. at room temperature. The mixture was concentrated in vacuo, the residue taken up into ethyl acetate and washed with saturated ammonium chloride solution. The organic layer was dried (sodium sulfate), filtered and concentrated in vacuo. Purification using reverse phase HPLC (eluent: acetonitrile/water/0.1% trifluoroacetic acid) provided 26 mg of N-Naphtho[1,2-d]thiazol-2-yl-isonicotinamide 22. ES-HRMS m/e calcd for C17H11N3OS (M+H) 306.0696, found 306.0691.

Provenance & Evidence