Dimethylformamide → HCID 86700240, compound

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Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-ethylpiperazin-1-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (26.7 mg, 0.044 mmol), 5M NaOH (176 μL, 0.879 mmol)) in methanol (0.2 mL) and THF (1.0 mL) was stirred at 45° C. for 2 h, then stirred overnight at rt. Acetic acid (1 drop) and DMF (0.3 mL) were added and mixture concentrated to ˜0.3 mL, diluted with methanol, 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 C31H36ClN4O3S: 579.2 (M+H+); Found: 579.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.27 (d, J=5.4 Hz, 1H), 7.84 (s, 1H), 7.66 (dd, J=8.5, 1.7 Hz, 1H), 7.63-7.52 (m, 3H), 7.50 (s, 1H), 7.32 (dd, J=5.4, 1.3 Hz, 1H), 5.25 (s, 1H), 4.81-4.18 (m, 2H), 4.81-4.18 (m, 2H), 3.7-2.99 (m, 4H), 3.27 (dd, J=14.8, 7.5 Hz, 3H), 2.59 (s, 3H), 1.39 (t, J=7.3 Hz, 3H), 0.96 (s, 9H).

Provenance & Evidence