2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide → 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide

Participants

Reaction Steps

Compound 32A was prepared from compound 26A as follows. To a solution of 2-[6-nitrobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (280 mg, 0.73 mmol) in MeOH (25 mL) was added a slurry of 10% palladium on carbon (200 mg) in MeOH (10 mL), and the mixture was stirred under hydrogen at atmospheric pressure for 24 hr. The mixture was filtered and the filtrate concentrated to give crude 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide as a red powder. This was purified by flash column chromatography eluting with 19:1 EA/MeOH to give pure 2-[6-aminobenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide, compound 32A (160 mg, 62% yield) as a yellow powder.

Provenance & Evidence