1,2-Dichloroethane → HCID 68082872, compound

Participants

Reaction Steps

1-(1-Methylethyl)-3-nitro-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (24 mg, 0.074 mmol), 3-(aminomethyl)-4,6-dimethyl-2(1H)-pyridinone hydrochloride (18 mg, 0.096 mmol), HOAT (17 mg, 0.110 mmol) and EDC (21 mg, 0.110 mmol) were suspended in DMSO (800 μL) and the reaction mixture stirred at room temperature. Next added 4-methylmorpholine (41 μl, 0.368 mmol), and the reaction was stirred at room temperature for 16 h. The reaction mixture was added dropwise to cold, slightly basic solution of water (3 mL) and 1N Na2CO3 (0.5 mL). After stirring for 20 min., the precipitated solids were collected via vacuum filtration and washed with water. The solid was dried on the high vacuum (72 h). The product, was collected as an off-white powder (28 mg, 82%). LCMS E-S (M+H)=461.1. 1H NMR (400 MHz, DMSO-d6) δ 9.01 (br. s., 1H), 8.42 (s, 1H), 8.02 (ddd, J=1.14, 4.99, 7.77 Hz, 2H), 7.99 (s, 1H), 7.86 (td, J=1.26, 7.58 Hz, 1H), 7.72-7.77 (m, 1H), 5.90 (s, 1H), 5.04 (quin, J=6.69 Hz, 1H), 4.41 (d, J=4.55 Hz, 1H), 3.34 (s, 2H), 2.22 (s, 3H), 2.12 (s, 3H), 1.49 (d, J=6.57 Hz, 6H).

Provenance & Evidence