1,2-Dichloroethane → HCID 67812886, compound

Participants

Reaction Steps

3-Isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxylic acid (80.7 mg, 0.27 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (66.2 mg, 0.35 mmol) and 1-hydroxy-7-azabenzotriazole (56.7 mg, 0.42 mmol) were stirred in 3 mL of DMSO for 10 min under nitrogen. N-methylmorpholine (0.12 mL, 1.09 mmol) was added along with EDC (78.3 mg, 0.41 mmol) and the mixture was stirred at room temperature for 19 hours. Ice-water (15 mL) and a concentrated solution of potassium carbonate were added to pH 10 and the solution was stirred for 40 minutes at room temperature. The solids were filtered, washed with water and dried. DMF was added along with water, solids were filtered and dried in vacuum-oven overnight to give N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-isopropyl-1-methyl-5-(methylsulfonyl)-1H-indole-7-carboxamide (88 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.31 (d, J=6.8 Hz, 6H) 2.12 (s, 3H) 2.24 (s, 3H) 3.18-3.26 (m, 4H) 3.71-3.75 (m, 3H) 4.36 (d, J=4.80 Hz, 2H) 5.89 (s, 1H) 7.33 (s, 1H) 7.51 (d, J=1.77 Hz, 1H) 8.14 (d, J=2.02 Hz, 1H) 8.65 (t, J=4.93 Hz, 1H) 11.52 (s, 1H). MS (ES) [M+H]+ 430.3.

Provenance & Evidence