Dimethylformamide → (1R,5S)-3-(4-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)pyrimidin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxamide

Participants

Reaction Steps

In a 4 mL vial equipped with a magnetic stir bar were mixed (1R,5S)-3-(4-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)pyrimidin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (80 mg, 0.198 mmol), NH4Cl (21.22 mg, 0.397 mmol), HATU (90 mg, 0.238 mmol) and Et3N (0.083 mL, 0.595 mmol) in DMF (2 mL). The resulting brown solution was stirred overnight. The product was purified by preparative HPLC, eluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a white solid (3.3 mg, 3.2%). 1H NMR (400 MHz, CD3OD) δ ppm 0.78-0.86 (m, 2H), 1.88 (ddd, J=12.06, 7.26, 4.67 Hz, 1H), 2.09-2.15 (m, 1H), 2.25-2.29 (m, 3H), 3.82 (dd, J=10.61, 5.05 Hz, 1H), 3.92-3.96 (m, 1H), 4.61 (d, J=5.31 Hz, 1H), 7.28 (d, J=1.01 Hz, 1H), 7.93-7.95 (m, 2H), 8.27 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C19H17F3N6O, 403.2. found 403.4.

Provenance & Evidence