Ethanolamine → HCID 131730180, compound

Participants

Reaction Steps

cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.095 g, 0.28 mmol) and 4-nitrophenyl chloroformate (0.29 mmol) were dissolved in DCM (4 mL) and TEA (0.3 mmol) and the resulting mixture stirred overnight. The mixture was diluted with DCM (25 mL) and washed with aqueous citric acid (10% w/v) and saturated aqueous sodium hydrogen carbonate and then brine. After drying with magnesium sulphate, the mixture was filtered and the solvent evaporated to give a clear gum. DCM (3 mL) was added together with 2-aminoethanol (0.26 mmol). The mixture was refluxed overnight and then diluted with DCM (10 mL) and washed with aqueous citric acid (10% w/v) and 2M aqueous sodium carbonate and then brine. After drying with magnesium sulphate, the mixture was filtered and the solvent evaporated to give a yellow gum which was purified by HPLC eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (0.055 g). LCMS m/z 420.30 [M+H]+ RT=8.68 min (Analytical Method 2).

Provenance & Evidence