Acetic Acid → HCID 86700269, compound

Participants

Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(1,3-dimethyl-1H-pyrazolo[3,4-c]pyridin-5-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (17.9 mg, 0.032 mmol)and 5M NaOH (0.127 mL, 0.636 mmol) in MeOH (0.2 mL) and THF (1.2 mL) was stirred at 50° C. for 3 hours, then stored in freezer overnight. DMF (0.3 mL) and acetic acid (0.011 mL) were added and reaction mixture was concentrated to ˜0.3 mL, filtered using a syringe filter, diluted with methanol. Purified using Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) and lyophilized to give desired product. LCMS-ESI+: calc'd for C28H28ClN4O3S: 535.2 (M+H+); Found: 535.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.83 (s, 1H), 8.45 (s, 1H), 7.73 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 7.57 (s, 1H), 5.26 (s, 1H), 4.02 (s, 3H), 2.59 (s, 3H), 2.53 (s, 3H), 0.97 (s, 9H).

Provenance & Evidence