Cyclohexanemethylamine → HCID 18790608, compound

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Reaction Steps

To a solution of the product of example 3 (358 mg, 1.0 mmol) in DMF (10 mL) were added successively cyclohexanemethylamine (130 μL, 1.0 mmol), DIPEA (700 μL, 4.0 mmol) and TBTU (321 mg, 1.0 mmol). The resulting mixture was stirred at room temperature for 18 h and then diluted with EtOAc. The mixture was washed with a saturated aqueous solution of NaHCO3 and then brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 4:1, EtOAc:hexane) to afford the title compound (300 mg, 87% yield) as a white solid: M.p. 145-147°; 1H NMR (400 MHz, DMSO-d6) δ 8.00 (broad t, J=6.0 Hz, 1H), 7.71 (d, J=8.7 Hz, 2H), 6.98 (s, 2H), 6.94 (d, J=8.7 Hz, 2H), 6.84 (s, 1H), 4.48 (s, 2H), 2.97 (t, J=6.4 Hz, 2H), 0.82-1.66 (m, 11H); MS (FAB) m/z 346 (MH)+. Anal. Calcd for C18H23N3O2S: C, 62.58; H, 6.71; N, 12.16. Found: C, 62.48; H, 6.74; N, 12.17.

Provenance & Evidence