Dimethylformamide → HCID 86700244, compound

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Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (35 mg, 0.052 mmol) and 5M sodium hydroxide (0.21 mL, 1.04 mmol) in methanol (0.3 mL) and THF (1.0 mL) was heated 45° C. for 2 h. 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 C31H29ClF3N6O3S: 657.2 (M+H+); Found: 657.3 (M+H1); NMR (400 MHz, CD3OD) δ 8.22 (d, J=5.5 Hz, 1H), 7.81 (s, 1H), 7.66 (dd, J=8.7, 1.8 Hz, 1H), 7.62-7.49 (m, J=10.0, 7.3 Hz, 4H), 7.32 (dd, J=5.5, 1.3 Hz, 1H), 5.24 (s, 1H), 5.07 (s, 2H), 4.36 (t, J=5.2 Hz, 2H), 4.20 (t, J=5.3 Hz, 2H), 2.57 (s, 3H), 0.95 (s, 9H).

Provenance & Evidence