Trimethylsilyl isocyanate → HCID 86646714, compound

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Reaction Steps

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.053 g, 0.16 mmol) in DCM (1 mL) was added trimethylsilylisocyanate (1.6 mmol). The mixture was stirred at room temperature overnight and then more trimethylsilylisocyanate (1.6 mmol) was added and the mixture stirred for a further 5 hours. The solution was diluted with DCM (10 mL) and washed with water. The resulting organic solution was dried and the solvent evaporated. The resulting oil 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 as a colourless oil (0.014 g). LCMS m/z 376.12 [M+H]+ RT=8.89 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.25 (s, 1H), 6.9 (s, 1H), 4.7 (s, 2H), 4.6 (m, 1H), 4.1 (m, 2H), 3.8 (m, 1H), 3.2-2.7 (m, 4H), 2.1-1.05 (m, 17H).

Provenance & Evidence