Acetic Anhydride → HCID 15407882, compound

HRID 479748Notes

Reaction equation

HRID 479748 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:26])[C:11]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:26])[C:11]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 9902528HCID 9902528, compound

Product 1

HCID 15407882HCID 15407882, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-aminomethylphenyl)-1-methyl -4-phenyl-5-(4-pyridyl)imidazole (30 mg, 0.09 mmol) [See Ex. 4 above] in pyridine (3 mL) was added acetic anhydride (0.30 mL, 3.18 mmol). The resulting solution was stirred at rt for 30 min, then concentrated under reduced pressure. The residue was purified by flash chromatography, eluting with a solvent gradient of 0-2% MeOH/CHCl3. The isolated material was triturated with Et2O to provide an off-white solid (10 mg, 28%) which was recrystallized from EtOAc to provide the title compound: mp 210-211° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography
  3. washeluting with a solvent gradient of 0-2% MeOH/CHCl3
  4. customThe isolated material was triturated with Et2O

Sources & evidence

ORD record
ord-aa9e770fba65460b94124178aaad9b9f
Source dataset
uspto-grants-2003_11
Patent number
US06645989B2

Reaction notes

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