Diethyl Pyrocarbonate → 1-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]-N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide

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Reaction Steps

A solution of acid 18 (0.50 g, 1.62 mmol) in THF (25 mL) was added with DEPC (0.32 mL, 1.3 mol eq) and the mixture was stirred at room temperature for 10′. Then [2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 21B (0.47 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, water (40 mL) was added to the residue that was extracted with EtOAc (3×25 mL) and washed with brine (1×40 mL). The separated organic phase was dried over Na2SO4, evaporated to dryness and the residue was purified by flash chromatography (1:1 EtOAc:Petroleum ether) to afford a pale yellow oil (0.31 g). Yield=35%, 1HNMR (DMSO, 200 MHz) δ 1.22 (t, 3H), 1.40 (bs, 2H), 1.61 (bs, 2H), 4.16 (q, 2H), 4.42 (d, 2H, J=6.1), 7.26 (m, 2H), 7.46 (d, 2H, J=8), 7.6 (dd, 1H), 7.87 (s, 1H), 8.21 (d, 2H, J=7.9), 8.25 (t, 1H), 8.60 (d, 1H, J=4); [M+1] 560.01 (C23H21ClF3N3O4S2 requires 559.06).

Provenance & Evidence