Acetic Anhydride → HCID 178474883, compound

HRID 658117Notes

Reaction equation

HRID 658117 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:6]=[C:7]([C:11](=[O:32])[C:12](=[C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[NH:24]2)[C:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)=[O:14])[CH:8]=[CH:9][CH:10]=1)[OH:4].[C:33](OC(=O)C)(=[O:35])[CH3:34].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[F:22][C:17]1[CH:16]=[C:15]([C:13](=[O:14])[C:12](=[C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[NH:24]2)[C:11]([C:7]2[CH:6]=[C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:33](=[O:35])[CH3:34])[CH:10]=[CH:9][CH:8]=2)=[O:32])[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 178511391HCID 178511391, compound

Product 1

HCID 178474883HCID 178474883, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A 137 mg portion of 1-[3-(2-amino-1-hydroxyethyl)phenyl]-3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)propane-1,3-dione was dissolved in 10 ml of pyridine, and 35 mg of acetic anhydride was added thereto under ice-cooling. After 2.5 hours of stirring at room temperature, the reaction liquid was mixed with an appropriate amount of sodium bicarbonate aqueous solution, extracted with ethyl acetate, dried with anhydrous sodium sulfate and concentrated, and then the thus formed residue was purified by a silica gel column chromatography to obtain 120 mg (80%) of N-(2-{3-[3-(3,5-difluorophenyl)-2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-3-oxopropanoyl]phenyl}-2-hydroxyethyl)acetamide (Example 15-1) as a yellow foam from a chloroform-methanol (30:1) eluate. FA: 478

Workup

  1. temperatureunder ice-cooling
  2. customthe reaction liquid
  3. extractionextracted with ethyl acetate
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe thus formed residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-06a93773cd554bbdbf3245bc595203e5
Source dataset
uspto-grants-2011_12
Patent number
US08076367B2

Reaction notes

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