Acetic Anhydride → HCID 9917671, compound

HRID 1005589Notes

Reaction equation

HRID 1005589 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:45]=[CH:44][CH:43]=[CH:42][C:7]=1[C:8]([NH:10][C:11]1[CH:41]=[CH:40][C:14]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[O:31])=[O:16])=[CH:13][CH:12]=1)=[O:9].C(N(CC)CC)C.[C:53](OC(=O)C)(=[O:55])[CH3:54]>ClCCl>[C:53]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:45]=[CH:44][CH:43]=[CH:42][C:7]=1[C:8]([NH:10][C:11]1[CH:41]=[CH:40][C:14]([C:15]([N:17]([CH3:39])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]2)=[O:31])=[O:16])=[CH:13][CH:12]=1)=[O:9])(=[O:55])[CH3:54]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11104071HCID 11104071, compound

Product 1

HCID 9917671HCID 9917671, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled solution of 4-[2-[(3-aminoprop-1-yl)oxy]benzoyl]amino-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (200 mg) in dichloromethane (10 ml) were added triethylamine (36.2 mg) and acetic anhydride (36.5 mg) and the mixture was stirred at ambient temperature for 4 hours. The reaction mixture was washed successively with water (10 ml), saturated aqueous sodium hydrogen carbonate solution (10 ml) and brine (10 ml), and dried over magnesium sulfate. The solvent was evaporated to give 4-[2-[(3-acetylaminoprop-1-yl)oxy]benzoyl]amino-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (201 mg) as a colorless amorphous.

Workup

  1. washThe reaction mixture was washed successively with water (10 ml), saturated aqueous sodium hydrogen carbonate solution (10 ml) and brine (10 ml)
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5cde0b845ced491ebb75b9af02453849
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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