Trifluoroacetic acid → HCID 86719974, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-(methoxymethyl)-6-{1-[1-(5-{2-(tetrahydro-2H-pyran-2-yloxy)ethoxy}pyridine-2-yl)-1H-pyrazol-3-yl]ethyl}-3H-1,3-benzothiazol-2-one (140 mg, 274.18 μmoles) in trifluoroacetic acid (0.05 M; 73 mmoles; 5.5 mL) and heat at reflux (˜72° C.) under N2 for 2 hr. (orange color observed after about 10 min. and at 70° C.). Cool the reaction to room temperature and concentrate under reduced pressure. Dissolve the residue in THF (0.05 M; 67 mmoles, 5.5 mL), add 28% ammonium hydroxide (0.2 M; 9.9 mmoles; 1.4 mL), and stir at room temperature for ˜1 hr. Dilute with EtOAc (100 ml), wash with brine, dry over sodium sulfate, filter and concentrate. Purify by liquid chromatography on a 25 g silica gel column, eluting with a gradient of 60-80% EtOAc in hexanes to give 6-(1-{1-[5-(2-hydroxy-ethoxy)-pyridin-2-yl]-1H-pyrazol-3-yl}-ethyl)-3H-1,3-benzothiazol-2-one as a white foam (80 mg; 209 μmoles; 76% yield). LCMS (Low) rt 1.8 min., M+1=383.

Provenance & Evidence