1,1'-Carbonyldiimidazole → 3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl ester

HRID 1747309Notes

Reaction equation

HRID 1747309 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[NH2:18])[CH2:7][CH2:8][CH3:9])[CH3:2].C1N=CN([C:25](N2C=NC=C2)=[O:26])C=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH:6]([N:10]1[C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=2[NH:18][C:25]1=[O:26])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 594975033-(2-Amino-5-methyl-phenylamino)-hexanoic acid ethyl ester

Product 1

HCID 594972823-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-hexanoic acid ethyl esterYield 84.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(2-Amino-5-methyl-phenylamino)-hexanoic acid ethyl ester (1.4 g, 5.3 mmol) in THF (20 mL) was added CDI (1.0 g, 6.4 mmol). The reaction mixture was stirred at room temperature for 16 h. When the reaction was complete, the reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and concentrated to afford 1.3 g of the desired product as dark brown solid. The resulting residue was used for the next reaction without further purification. LCMS (ESMS): m/z 291.40 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9e0bbcee951f4a23b0e22b987dbd8ab3
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…