Triethylamine → 1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-n-(5-methyl-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

1-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)-N-(6′-methoxy-3-methyl-2,3′-bipyridin-6-yl)cyclopropanecarboxamide (482 mg, 1.10 mmol) was dissolved in a mixture of 6 mL of 1,4-dioxane and 3 mL of 4M aqueous hydrochloric acid. This solution was heated at 90° C. for 1.5 hours. The crude reaction mixture was quenched with one equivalent of triethylamine and then evaporated to dryness. The crude product was then partitioned between dichloromethane and water. The organic layer was separated, dried over sodium sulfate, and then purified on 12 g of silica gel utilizing a gradient of 0-10% methanol in dichloromethane to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)cyclopropanecarboxamide as a white solid (189 mg, 40%). ESI-MS m/z calc. 425.1. found 426.3 (M+1)+. Retention time 1.53 minutes. 1H NMR (400 MHz, DMSO-d6) δ 11.78 (s, 1H), 8.91 (s, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.66-7.64 (m, 2H), 7.56-7.55 (m, 2H), 7.41 (d, J=8.3 Hz, 1H), 7.34 (dd, J=1.7, 8.3 Hz, 1H), 6.36 (d, J=9.5 Hz, 1H), 2.28 (s, 3H), 1.52-1.49 (m, 2H), 1.18-1.15 (m, 2H).

Provenance & Evidence