Benzoyl isothiocyanate → HCID 178522520, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 4-bromo-5-(3-chloro-phenyl)-2H-pyrazol-3-ylamine (50 mg, 0.183 mmol) in dioxane (1 mL) was added benzoyl isothiocyanate (27 μL, 0.202 mmol). The reaction mixture was stirred overnight at 90° C., cooled at room temperature, and partitioned between ethyl acetate and sodium bicarbonate. The organic layer was isolated and absorbed on silica gel. Purification on silica gel with 0-10% MeOH in CH2Cl2 as eluent provided 10.8 mg (17%) of N-[3-(3-chloro-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-yl]-benzamide as a white solid. 1H NMR (d6-DMSO) δ: 13.70 and 13.72 (2 broad s, 1H, NH+tautomer), 12.9 (broad s, 1H, NH), 8.12 (d, 2H), 7.81 and 7.85 (2 broad s, 1H, tautomers), 7.65-7.74 (m, 2H), 7.54-7.62 (m, 3H), 7.45 (m, 1H); HPLC/MS m/z: 355 [MH]+.

Provenance & Evidence