Methylamine → HCID 86594248, compound

Participants

Reaction Steps

To a solution of 7-{[(1R)-3-iodo-1-phenylpropyl]oxy}-1-benzothiophene-2-carbonitrile (156 mg, 0.37 mmol) in tetrahydrofuran (1.5 mL) was added 40% aqueous methylamine (0.5 mL) and the solution was stirred at room temperature for 16 hours. The solvent removed in vacuo and the residue purified by flash chromatography with a gradient of 0–15% methanol in dichloromethane. To a solution of free base (96 mg, 0.3 mmol) in methanol (1 mL) and added a warm solution of fumaric acid (26 mg, 0.3 mmol) in methanol (1 mL). The solvent removed in vacuo, and the solid residue triturated with ether (5 mL), then dried in a vacuum oven at 40° C. for 1 hour to give the title compound (120 mg, 74%); δH (300 MHz, DMSO) 8.40 (1H, s, 3-ArH), 7.61–7.52 (1H, m, ArH), 7.49–7.23 (6H, m, ArH), 7.05–6.98 (1H, m, ArH), 6.45 (2H, s, CHCO2H), 5.85–5.75 (1H, m, CHO), 3.05–2.90 (2H, m, 1-CH2), 2.52 (3H, s, NHCH3) and 2.46–2.07 (2H, m, 2-CH2).

Provenance & Evidence