Acetic Acid → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetic acid

Participants

Reaction Steps

A solution of (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (7.7 mg, 0.012 mmol) and 5M sodium hydroxide (20 μL, 0.012 mmol) in THF (1 mL) and MeOH (0.2 mL) was stirred at 50° C. for 2 h. Reaction mixture was cooled to rt, acetic acid (15 μL) and DMF (0.3 mL) were added and reaction mixture was concentrated to ˜0.3 mL, filtered, purified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) and lyophilized to give desired product. LCMS-ESI+: calc'd for C32H30ClN6O3S: 613.2 (M+H+); Found: 613.2 (M+H+); 1H NMR (400 MHz, CD3OD) δ 9.41 (s, 1H), 9.28 (s, 1H), 8.85 (s, 1H), 8.25 (s, 1H), 7.99 (s, 1H), 7.76-7.43 (m, 4H), 5.28 (s, 1H), 4.16 (s, 3H), 2.71 (s, 3H), 2.65 (s, 3H), 0.98 (s, 9H).

Provenance & Evidence