Dimethylformamide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

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Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate (4.2 mg, 0.00724 mmol) 5M NaOH (29 μL) in methanol (0.2 mL) and THF (1.0 mL) was stirred at 40° C. overnight. Acetic acid (1 drop) and DMF (0.3 mL) were added and mixture concentrated to ˜0.5 mL, diluted with DMF/H2O, filtered and purified by Gilson HPLC (Gemini, 5 to 100% ACN/H2O+0.1% TFA) to give product after lyophilization. LCMS-ESI+: calc'd for C29H31ClN3O4S: 552.2 (M+H+); Found: 552.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.12 (d, J=6.2 Hz, 1H), 7.94 (s, 1H), 7.69 (s, 1H), 7.67 (d, J=2.1 Hz, 1H), 7.61 (d, J=2.1 Hz, 1H), 7.59 (dd, J=4.2, 2.1 Hz, 2H), 7.47 (dd, J=6.2, 1.5 Hz, 1H), 5.26 (s, 1H), 3.91-3.79 (m, 4H), 3.74-3.62 (m, 4H), 2.63 (s, 3H), 0.97 (s, 9H).

Provenance & Evidence