Ethyl Acetate → methyl (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylate

HRID 1515034Notes

Reaction equation

HRID 1515034 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([CH:34]=O)=[C:29]([CH3:36])[CH:28]=1.OOS([O-])=O.[K+].C(OCC)(=O)C>CN(C=O)C.O>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5]([C:4]2[CH:18]=[CH:19][C:20]3[N:21]=[C:34]([C:30]4[C:29]([CH3:36])=[CH:28][C:27](/[CH:26]=[CH:25]/[C:24]([O:23][CH3:22])=[O:37])=[CH:32][C:31]=4[CH3:33])[NH:1][C:2]=3[CH:3]=2)=[O:6])=[CH:9][CH:10]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 54209618Methyl 3-(3,5-dimethyl-4-formylphenyl)propionateHCID 669661113,4-diamino-N-(4-tert-butylphenyl)-benzamide

Product 1

HCID 66965696methyl (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-diamino-N-(4-tert-butylphenyl)-benzamide (1.83 g, 6.46 mmol) and 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester (1.55 g, 7.10 mmol) (from Example 6-17) in DMF (25 mL) and water (2.5 mL) was added oxone (2.66 g, 4.33 mmols) and the mixture was stirred at ambient temperature for 1 h. The mixture was poured into ethyl acetate, extracted once with water and five times with brine, and the organic layer was dried, filtered, and the solvent was removed under reduced pressure. The residue was chromatographed using a 50-90% gradient of heptane/ethyl acetate to give methyl (E)-3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-benzimidazol-2-yl]-3,5-dimethylphenyl}-acrylate.

Workup

  1. extractionextracted once with water and five times with brine
  2. customthe organic layer was dried
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-a1fadefcde8b4177ba9baa7dd6272e22
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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