2-Thiophenecarbonyl chloride → HCID 74344140, compound

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Reaction Steps

To a solution of (trans (+/−))-1-(1,4′-bipiperidin-4-yl)octahydro-2H-benzimidazol-2-one. 2TFA (180 mg, 0.31 mmol) in a mixture of dichloromethane and chloroform (1:4) was added diisopropylethylamine (0.2 mL, 1.1 mmol) followed by thiophene-2-carbonyl chloride (0.1 mL, 0.6 mmol) at room temperature. The mixture stirred 48 hours and then quenched with water. Diluted in dichloromethane (60 mL) and washed with 1N NaOH (5 mL) and brine (5 mL) and concentrated in vacuo. The crude was purified by high pH prep LCMS (acetonitrile/water) to provide 26 mg of the title compound as a white solid. 1H NMR (400 MHz, CHLOROFORM-D): δ ppm 1.26-1.58 (m, 6H), 1.59-2.03 (m, 9H), 2.12-2.34 (m, 3H), 2.44-2.64 (m, 1H), 2.82-3.06 (m, 6H), 3.62-3.84 (m, 1H), 4.29-4.57 (m, 2H), 4.63 (s, 1H), 7.01 (d, J=5.08 Hz, 1H), 7.18-7.27 (m, 1H), 7.35-7.46 (m, 1H). MS (M+1): 417.3

Provenance & Evidence