Dimethylformamide → HCID 86700242, compound

Participants

Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(4-isopropylpiperazin-1-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (36.7 mg, 0.059 mmol), 5M NaOH (236 μL, 1.18 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 DMF/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 C32H38ClN4O3S: 593.2 (M+H+); Found: 593.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.26 (d, J=5.5 Hz, 1H), 7.84 (s, 1H), 7.66 (dd, J=8.5, 1.8 Hz, 1H), 7.61-7.48 (m, 4H), 7.33 (dd, J=5.4, 1.3 Hz, 1H), 5.24 (s, 1H), 4.77-4.40 (m, J=33.2 Hz, 2H), 3.58 (td, J=13.2, 6.6 Hz, 1H), 3.50-3.14 (m, 2H), 2.58 (s, 3H), 1.41 (d, J=6.7 Hz, 6H), 0.95 (s, 9H).

Provenance & Evidence