Acetic Anhydride → HCID 67392943, compound

HRID 910624Notes

Reaction equation

HRID 910624 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:40])[C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:26](=[O:39])[N:27]([CH2:31][CH2:32][N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)[CH:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[N:6][CH:7]=1.[C:42](OC(=O)C)(=[O:44])[CH3:43]>N1C=CC=CC=1>[ClH:1].[C:42]([N:36]1[CH2:35][CH2:34][N:33]([CH2:32][CH2:31][N:27]2[CH:28]=[CH:29][CH:30]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([NH:17][C:11]4[C:12]([OH:16])=[CH:13][CH:14]=[CH:15][C:10]=4[C:9]([NH:8][C:5]4[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=4)=[O:41])=[O:40])=[CH:20][CH:21]=3)[C:26]2=[O:39])[CH2:38][CH2:37]1)(=[O:44])[CH3:43]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 57584073HCID 57584073, compound

Product 1

HCID 67392943HCID 67392943, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-(5-chloropyridin-2-yl)-3-hydroxy-2-({4-[2-oxo-1-(2-piperazin-1-ylethyl)-1,2-dihydropyridin-3-yl]benzoyl}amino)benzamide (128 mg) was dissolved in pyridine (5 mL), and acetic anhydride (21 μL) was added, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, then azeotroped twice with toluene. Water was added to the residue, followed by extraction with chloroform and drying over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 5%). The resulting compound was dissolved in ethyl acetate and 4 N hydrochloric acid/ethyl acetate was added. The precipitate formed was collected by filtration and dried under reduced pressure to obtain 2-[(4-{1-[2-(4-acetylpiperazin-1-yl)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoyl)amino]-N-(5-chloropyridin-2-yl)-3-hydroxybenzamide hydrochloride (109 mg) as a yellow white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customazeotroped twice with toluene
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with chloroform
  5. dry with materialdrying over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by NH-silica gel column chromatography (methanol/chloroform=0% to 5%)
  8. dissolutionThe resulting compound was dissolved in ethyl acetate
  9. addition4 N hydrochloric acid/ethyl acetate was added
  10. customThe precipitate formed
  11. filtrationwas collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-9015f5f31a904baa9eba6b29408f38b8
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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