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

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Reaction Steps

A solution of acid 4C (0.40 g, 1.45 mmol) in THF (25 mL) was added with DEPC (0.28 mL, 1.3 mol eq) and the mixture was stirred at room temperature for about 5 minutes. Then [2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 27D (0.56 g, 1.1 mol eq) and a catalytic amount of TEA were added, then the reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was suspended in EtOAc and washed with water and brine. After drying over Na2SO4, the separated organic phase was evaporated under reduced pressure and the residue was purified by flash chromatography (7:3 EtOAc:Petroleum ether) to afford a pale yellow solid (0.24 g) after crystallization from a mixture of diethyl ether/petroleum ether. Yield=36%, 1HNMR (DMSO, 200 MHz) δ 2.95 (s, 3H), 3.55 (m, 4H), 3.70 (m, 4H), 4.40 (d, 2H, J=6), 5.12 (s, 1H), 5.87 (s, 1H), 6.82 (s, 1H), 7.29 (s, 1H), 7.43 (d, 2H, J=8.2), 7.83-7.74 (m, 4H), 8.17 (d, 2H, J=8), 8.86 (t, 1H); [M+1] 611.03 (C27H26ClF3N4O5S requires 610.13).

Provenance & Evidence