Dichloromethane → HCID 178502020, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cis-4-(2-amino-5-(piperidin-1-ylmethyl)phenylamino)-N-isopropylcyclohexanecarboxamide (0.300 g, 0.805 mmol) in MeOH (4.5 mL) was added 1,3-bis(methoxycarbonyl)-2-methyl-2-thiopseudourea (0.166 g, 0.805 mmol) and p-toluenesulfonic acid monohydrate (0.168 g, 0.886 mmol). The reaction mixture was heated at 80° C. for 2 hours and then concentrated under vacuum. The residue was dissolved in DCM and was washed with saturated aqueous NaHCO3. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by flash chromatography, eluting with 0-100% 90:10:1 DCM/MeOH/NH4OH:DCM to afford methyl 1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(piperidin-1-ylmethyl)-1H-benzo[d]imidazol-2-ylcarbamate (0.239 g, 65.1% yield). MS, m/z (C25H37N5O3); calcd, 455.59. found 456.2 [M+H]. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (d, J=6.55 Hz, 6H) 1.38-1.49 (m, 2H) 1.52-1.67 (m, 4H) 1.67-1.85 (m, 6H) 2.10-2.20 (m, 2H) 2.34-2.51 (m, 4H) 2.58-2.73 (m, 2H) 3.54-3.66 (m, 1H) 3.79 (s, 3H) 4.20 (dt, J=13.70, 6.70 Hz, 1H) 4.86 (tt, J=12.79, 4.47 Hz, 1H) 5.34 (br. d, J=7.20 Hz, 1H) 7.13-7.25 (m, 2H) 7.61 (br. s., 1H) 11.29 (br. s., 1H).

Provenance & Evidence