Dimethylcarbamoyl Chloride → HCID 71472665, compound

Participants

Reaction Steps

To a solution of 6-(4-hydroxybenzyl)-3-[(1S,2S)-2-hydroxycyclohexyl]-10-methyl-9,10-dihydropyrido[3,2-h]quinazolin-4(3H)-one (Example 7, 0.025 g, 0.060 mmol) in 2 mL of dichloromethane at 0° C. was added triethylamine (0.012 mL, 0.090 mmol) and dimethyl carbamyl chloride (0.010 g, 0.090 mmol). After 2 h, the mixture was warmed to rt and additional dimethyl carbamyl chloride (0.019 g, 0.18 mmol) was added. After 20 h, the reaction was warmed to 35° C., and after an additional 36 h, diluted with dichloromethane and washed with water and brine. The organic solution was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-3% methanol in dichloromethane, to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 489.1 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 3.24 (d, J=8.4 Hz, 1H), 8.03 (s, 1H), 7.41-7.38 (m, 1H), 7.14 (d, J=7.9 Hz, 2H), 7.01-6.98 (m, 2H), 4.77-4.64 (m, 2H), 4.37 (s, 2H), 3.64 (br s, 1H), 3.27 (s, 3H), 3.06 (s, 3H), 2.98 (s, 3H), 2.22-2.19 (m, 1H), 2.12-2.09 (m, 1H), 1.91 (br s, 1H), 1.82 (br s, 1H), 1.64-1.60 (m, 1H), 1.49-1.25 (m, 4H).

Provenance & Evidence