Dimethylformamide → HCID 86700248, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(1,3-dimethyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate: A mixture of 1,3-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (7.7 mg, 0.012 mmol) and 5M sodium hydroxide (47 μL, 0.24 mmol) in methanol (0.1 mL) and THF (0.5 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 C32H34ClN5O3S: 616.2 (M+H+); Found: 616.3 (M+H+); 1H NMR (400 MHz, CD3OD) δ 8.11 (d, J=6.3 Hz, 1H), 7.96 (s, 1H), 7.83 (s, 1H), 7.68 (dd, J=8.5, 1.7 Hz, 1H), 7.67-7.54 (m, 3H), 7.47 (dd, J=6.3, 1.3 Hz, 1H), 5.27 (s, 1H), 4.63 (s, 2H), 4.07 (t, J=5.7 Hz, 2H), 3.72 (s, 3H), 2.93 (t, J=5.5 Hz, 2H), 2.64 (s, 3H), 2.24 (s, 3H), 0.97 (s, 9H).

Provenance & Evidence