Sodium methanethiolate → HCID 70652423, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-5,6,7,8-tetrahydroquinoline-2-carboxamide trifluoromethyl acetate (0.060 g, 0.18 mmol) in 1 mL of DMSO was added sodium thiomethoxide (9.8 mg, 0.14 mmol). The mixture was heated at 80° C. for 1 h, at 90° C. for 1 h, then cooled to rt. After 15 h, additional sodium thiomethoxide (9.3 mg, 0.14 mmol) was added and the mixture was heated at 100° C. for 1 h, then cooled to rt. The mixture was diluted with ethyl acetate, washed 2× with water and 1× with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 35-85% ethyl acetate in hexanes, to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 412.0 for [M+H]+: 1H NMR (400 MHz, d6-DMSO) δ 8.32 (s, 1H), 8.14 (d, J=8.0 Hz, 1H), 7.53 (s, 1H), 5.43-7.40 (m, 1H), 7.25 (d, J=8.2 Hz, 1H), 4.67 (d, J=5.5 Hz, 1H), 4.02 (s, 2H), 3.54-3.48 (m, 1H), 3.43-3.37 (m, 1H), 3.00 (br s, 2H), 2.72 (br s, 2H), 1.91-1.87 (m, 2H), 1.79 (s, 3H), 1.65-1.59 (m, 2H), 1.24-1.17 (m, 3H).

Provenance & Evidence