Water → HCID 69454567, compound

HRID 916087Notes

Reaction equation

HRID 916087 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][S:12][C:13]1[NH:14][C:15]2[C:21](CC(O)=O)=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)=[O:4].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCN=C=NC[CH2:39][CH2:40]N(C)C.[OH2:44]>O1CCCC1>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][S:12][C:13]1[N:17]([CH2:39][C:40](=[O:44])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178497634HCID 178497634, compound

Product 1

HCID 69454567HCID 69454567, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-((2-(methoxycarbonyl)phenyl)methylthio)benzimidazolyl)acetic acid (35 mg, 0.1 mmol) was dissolved in tetrahydrofuran (3 ml), to which aniline (11.2 mg, 0.12 mmol) and EDCI (23 mg, 0.12 mmol) were added, and then the mixture was stirred overnight at room temperature. Water was added thereto, followed by extraction with ethyl acetate. After drying with anhydrous sodium sulfate, it was filtered, the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:2) to obtain 2-((1-((N-phenylcarbamoyl)methyl)benzimidazole-2-ylthio)methyl)benzoic acid methyl ester (27.5 mg, yield 64%).

Workup

  1. additionwere added
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialAfter drying with anhydrous sodium sulfate, it
  4. filtrationwas filtered
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=3:2)

Sources & evidence

ORD record
ord-babf87fb963b4b0eaceed6ef4a861234
Source dataset
uspto-grants-2007_09
Patent number
US07268145B2

Reaction notes

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