Tetrahydrofuran → HCID 25211608, compound

Participants

Reaction Steps

Prepared from 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-cyanopiperidine by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and piperidine derivative. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a 1 N aqueous hydrochloric acid solution followed by water. The solid was air dried then chromatographed on a short column of silica gel with EtOAc as eluant to afford product as a colorless solid (91 mg, 61%). 1H NMR (CDCl3) 1.91-2.06 (m, 4H), 2.37 (d, J=1.3, 3H), 2.97-3.03 (m, 1H), 3.71-3.79 (m, 2H), 3.90-3.98 (m, 2H), 7.34 (d, J=4.0, 1H), 7.47 (d, J=4.0, 1H). 13C NMR 7.9, 26.5, 28.9, 43.6, 114.8, 118.7 (q, J=271), 120.8, 128.1, 129.5, 131.7, 139.4, 155.2 (q, J=40), 157.8, 162.9. 19F NMR −63.2. LC/MS 6.18 min, [M+1]+ 370.

Provenance & Evidence