1,2-Dichloroethane → HCID 17393134, compound

Participants

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 6-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (60 mg, 0.27 mmol) and 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone.HCl (62 mg, 0.33 mmol) in DMSO (3 mL). 1-hydroxy-7-azabenzotriazole (56 mg, 0.41 mmol) was added and the resulting mixture was degassed with nitrogen for 10 minutes. N-methylmorpholine (0.11 ml, 0.96 mmol) and EDC (79 mg, 0.41 mmol) were added, the vessel was sealed, and the light brown mixture was stirred at room temperature for 2 days. Next added 2 mL of water and the mixture was stirred for 10 min. Solids that precipitated were sonicated, and allowed to stand at room temperature for 10 min. The contents were filtered, washed with water, and dried to afford the title compound (68 mg, 68%) as a light pink solid. LCMS E-S (M+H)=354.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.54 (s, 1H), 8.69 (t, J=4.80 Hz, 1H), 8.26 (s, 1H), 7.46 (s, 1H), 5.89 (s, 1H), 5.20 (quin, J=6.69 Hz, 1H), 4.36 (d, J=5.05 Hz, 2H), 2.63 (s, 3H), 2.21 (s, 3H), 2.13 (s, 3H), 1.48 (d, J=6.57 Hz, 6H).

Provenance & Evidence