1,2-Dichloroethane → HCID 22181274, compound

HRID 1796517Notes

Reaction equation

HRID 1796517 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([NH:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27]CC)=[CH:23][CH:22]=2)[CH3:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:30]([N:33]=[C:34]=[O:35])([CH3:32])[CH3:31].Cl[CH2:37][CH2:38]Cl>>[CH:1]1([CH2:7][N:8]2[C:12]3[CH:13]=[CH:14][C:15]([N:17]([CH3:18])[C:34]([NH:33][CH:30]([CH3:32])[CH3:31])=[O:35])=[CH:16][C:11]=3[N:10]=[C:9]2[CH:19]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:37][CH3:38])=[CH:25][CH:26]=2)[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 61277Isopropyl isocyanateHCID 22181424HCID 22181424, compound

Product 1

HCID 22181274HCID 22181274, compoundYield 58%

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(cyclohexylmethyl)-2-[1-(4-ethoxyphenyl)ethyl]-N-methyl-1H-benzimidazol-5-amine (2.1 g, 5.4 mmol) in 1,2-dichloroethane (270 mL) was added isopropyl isocyanate (1.1 mL, 10.8 mmol) at room temperature and the reaction mixture was heated at 60° C. overnight. The solution was cooled to room temperature, the solvent was evaporated and the brown residue was purified by MPLC (EtOAc on silica gel) to afford the title compound as a beige foam (1.5 g, 58%). 1H NMR (400 MHz, CD3OD) δ 0.95–1.18 (m, 11H), 1.36 (t, J =7.0 Hz, 3H), 1.41–1.68 (m, 6H), 1.82 (d, J=7.0 Hz, 2H), 3.31 (s, 3H), 3.89–3.95 (m, 1H), 4.01 (apq, J=7.0 Hz, 2H), 4.13–4.18 (m, 1H), 4.68 (q, J=7.2 Hz, 1H), 7.17–7.20 (m, 2H), 7.35 (dd, J=2.0, 8.8 Hz, 1H), 7.63 (d, J=2.0 Hz, 1H), 7.71 (d, J=8.8 Hz, 1H). MS (ESI) (M+H)+=477.48 (M+1)+. Anal. Calcd for C29H40N4O2+0.5HCl+0.8 CH3OH: C, 68.76; H, 8.46; N, 10.26. Found: C, 68.75; H, 8.61; N, 10.98.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customthe solvent was evaporated
  3. customthe brown residue was purified by MPLC (EtOAc on silica gel)

Sources & evidence

ORD record
ord-03fc0d4d8f7d4407b21340a7ee01b35a
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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