1,1'-Carbonyldiimidazole → [1-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl]-acetic acid methyl ester

HRID 1747401Notes

Reaction equation

HRID 1747401 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1COCC1>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][C:20]2=[O:21])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59497703[1-(2-Amino-phenylamino)-cyclohexyl]-acetic acid methyl ester

Product 1

HCID 59497625[1-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl]-acetic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(2-amino-phenylamino)-cyclohexyl]-acetic acid methyl ester (205 mg, 0.79 mmol) in THF (5 mL) was added 1,1′-carbonyldiimidazole (180 mg, 1.11 mmol). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated. The resulting residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent to afford the desired [1-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-cyclohexyl]-acetic acid methyl ester (194 mg, 86%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by CombiFlash with 50% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-985061a02aab4977a9141eb362673d9e
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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