1,1'-Carbonyldiimidazole → 4-Methoxy-2,2-dimethyl-3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-butyric acid methyl ester

HRID 1747405Notes

Reaction equation

HRID 1747405 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[CH:5]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16])[CH2:6][O:7][CH3:8].[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1COCC1>[CH3:1][O:2][C:3](=[O:19])[C:4]([CH3:17])([CH3:18])[CH:5]([N:9]1[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:20]1=[O:21])[CH2:6][O:7][CH3:8]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 594976723-(2-Amino-phenylamino)-4-methoxy-2,2-dimethyl-butyric acid methyl ester

Product 1

HCID 673585034-Methoxy-2,2-dimethyl-3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-butyric acid methyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-amino-phenylamino)-4-methoxy-2,2-dimethyl-butyric acid methyl ester (550 mg, 2.1 mmol) in THF (25 mL) was added 1,1′-carbonyldiimidazole (500 mg, 3.1 mmol). The solution was stirred at room temperature for 16 hours. The reaction mixture was concentrated. The resulting residue was purified by CombiFlash with 75% EtOAc in Hexane as the eluent to afford the desired 4-methoxy-2,2-dimethyl-3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-butyric acid methyl ester (420 mg, 70%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe resulting residue was purified by CombiFlash with 75% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-3eef6658094b4d298414580c3b1cf5d1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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