Diethyl Pyrocarbonate → (Z)-2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]but-2-enamide

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Reaction Steps

Acid 11B (574 mg, 2 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.3 ml) and [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (1.1 equiv., 590 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (1:1 EtOAc:petroleum ether) afforded 195 mg of a white solid. Yield=18% 1HNMR (DMSO, 200 MHz) δ 1.00 (3H, t, J=7.2 Hz), 1.46 (3H, d J=7.4 Hz), 3.43 (2H, q, J=7 Hz), 4.40 (2H, d, J=6 Hz), 6.83 (1H, q, J=7 Hz), 7.25 (1H, dd, J=6.4 Hz), 7.42 (4H, m), 7.85 (3H, m), 8.18 (2H, d, J=8.2 Hz), 8.60 (1H, d, J=5 Hz), 8.74 (1H, bt) [M+1] 538.1 (C25H23F4N3O4S requires 537.53).

Provenance & Evidence