Acetic Anhydride → HCID 23025766, compound

HRID 1437486Notes

Reaction equation

HRID 1437486 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[NH:15][C:14]([CH2:16][CH2:17][C:18]4[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=4)=[N:13][C:10]3=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C([O-])(=O)C.[NH4+]>N1C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]3[NH:15][C:14]([CH2:16][CH2:17][C:18]4[CH:19]=[CH:20][C:21]([NH:22][C:25](=[O:27])[CH3:26])=[CH:23][CH:24]=4)=[N:13][C:10]3=[N:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517165Ammonium AcetateHCID 23025741HCID 23025741, compound

Product 1

HCID 23025766HCID 23025766, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(2-(6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl)aniline (Compound of Example 589) (25 mg) and acetic anhydride (0.01 ml) in pyridine was stirred at room temperature for 6 hours, and the reaction mixture was poured onto ice. The mixture was neutralized with a 5% aqueous solution of ammonium acetate and extracted with ethyl acetate. The organic layer was washed with water and dried over Na2SO4. The solvent was distilled off and the resulting crystals were collected by filtration to obtain N-(4-(2-(6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl)phenyl)acetamide (22 mg, 78%).

Workup

  1. additionthe reaction mixture was poured onto ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent was distilled off
  6. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-fabde744919c475aaaf2faf2dc156342
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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