Diethyl Pyrocarbonate → 2-[(4-chlorophenyl)sulfonyl-ethyl-amino]-N-[[2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

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Reaction Steps

Acid 4D (289.74 mg, 1 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.15 ml) and [2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 27D (1.1 equiv., 388 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 (3:7 EtOAc:petroleum ether) afforded 140 mg of a pale yellow solid. Yield=22% 1HNMR (DMSO, 400 MHz) δ 1.15 (3H, t), 3.38 (2H, q), 3.50 (4H, m), 3.70 (4H, m), 4.40 (2H, d), 5.20 (1H, s), 6.18 (1H, s), 6.80 (1H, s), 7.20 (1H, s), 7.42 (2H, d), 7.76 (2H, d), 7.82 (2H, d), 8.18 (2H, d), 8.89 (1H, bt) [M+1] 626.9 (C28H28ClF3N4O5S requires 625.06).

Provenance & Evidence