1,1'-Carbonyldiimidazole → 1-Cyclohexylmethyl-6-(4-methyl-piperazin-1-yl)-5-phenylamino-1,3-dihydro-benzoimidazol-2-one

HRID 1241936Notes

Reaction equation

HRID 1241936 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[C:10]([NH2:29])=[CH:11][C:12]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30](N1C=CN=C1)(N1C=CN=C1)=[O:31]>C1COCC1>[CH:1]1([CH2:7][N:8]2[C:9]3[CH:14]=[C:13]([N:15]4[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]4)[C:12]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:11][C:10]=3[NH:29][C:30]2=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21061668N1-cyclohexylmethyl-5-(4-methyl-piperazin-1-yl)-N4-phenyl-benzene-1,2,4-triamine

Product 1

HCID 219377491-Cyclohexylmethyl-6-(4-methyl-piperazin-1-yl)-5-phenylamino-1,3-dihydro-benzoimidazol-2-oneYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N1-cyclohexylmethyl-5-(4-methyl-piperazin-1-yl)-N4-phenyl-benzene-1,2,4-triamine (0.10 g, 0.25 mmol) and 1,1′-carbonyldiimidazole (0.12 g, 0.76 mmol) in THF (3 mL) was stirred at room temperature for 17.5 h. The solvent was evaporated and the resulting residue was chromatographed (FCC, 5% MeOH/CH2Cl2) to give the title compound as a white solid (0.07 g, 61.6% yield). M+, 420.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting residue was chromatographed (FCC, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d6d5c6937931478085b2ab844a66e689
Source dataset
uspto-grants-2006_10
Patent number
US07115644B2

Reaction notes

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