1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → {4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester

HRID 1515037Notes

Reaction equation

HRID 1515037 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[CH:22]=[C:21]([C:23]([OH:25])=O)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[C:9]([CH3:26])[CH:8]=1)=[O:4].[C:27](NC1C=CC=CC=1)([CH3:30])([CH3:29])[CH3:28].CCN=C=NCCCN(C)C.[CH:49]1[CH:50]=[CH:51][C:52]2N(O)N=[N:55][C:53]=2[CH:54]=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH3:26])[C:10]([C:14]2[NH:15][C:16]3[CH:22]=[C:21]([C:23](=[O:25])[NH:55][C:53]4[CH:54]=[CH:49][C:50]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:51][CH:52]=4)[CH:20]=[CH:19][C:17]=3[N:18]=2)=[C:11]([CH3:13])[CH:12]=1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 254260N-(1,1-Dimethylethyl)benzenamineHCID 669656912-(4-methoxycarbonylmethoxy-2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid

Product 1

HCID 66965814{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-methoxycarbonylmethoxy-2,6-dimethylphenyl)-3H-benzoimidazole-5-carboxylic acid (0.3 g, 0.847 mmol) in DMF (6 mL) was added t-butylaniline (0.1338 mL, 0.847 mmol), EDCI (0.1953 g, 1.02 mmol) and HOBt (0.1374 g, 1.02 mmol). The brown solution was stirred at ambient temperature for 18 h. The mixture was extracted with EtOAc, then washed with water, brine, and dried with Na2SO4. The solvent was removed under reduced pressure and the residue purified on silica gel using MeCN/methylene chloride (1:1) to give {4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzoimidazol-2-yl]-3,5-dimethylphenoxy}-acetic acid methyl ester.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with water, brine
  3. dry with materialdried with Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified on silica gel

Sources & evidence

ORD record
ord-3dc47eda7f9947dbb9742f78536138fb
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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