Triethylamine → HCID 86617871, compound

Participants

Reaction Steps

To a solution of N-(4-(hydroxymethyl)-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide (480 mg, 1.53 mmol) in dichloromethane (10 mL) and DMSO (2.5 mL) was added triethylamine (1.07 mL, 7.66 mmol) and SO3-pyridine (975 mg, 6.13 mmol). The reaction mixture was stirred at rt for 0.5 h, diluted with EtOAc, washed with 1N HCl, sat'd aq NaHCO3, brine, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica, 25-50% EtOAc/hexanes) to provide N-(4-formyl-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-methylmethanesulfonamide. 1H NMR (400 MHz, CDCl3) δ 9.94 (s, 1H), 6.92 (s, 1H), 6.72 (s, 1H), 3.53 (A of ABX, dd, J=14.8, 6.4 Hz, 1H), 3.40 (s, 3H), 3.36 (B of ABX, dd, J=14.8, 6.8 Hz, 1H), 3.15 (s, 3H), 3.13 (s, 3H), 1.04 (d, J=6.0 Hz, 3H), 0.78-0.62 (m, 2H), 0.45-0.37 (m, 1H), 0.31-0.24 (m, 1H).

Provenance & Evidence