Acetic Acid → HCID 18355064, compound

HRID 429633Notes

Reaction equation

HRID 429633 reaction equation
[NH2:1][C:2]1[C:44]([NH2:45])=[CH:43][CH:42]=[CH:41][C:3]=1[C:4]([NH:6][C:7]1[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])=[O:12])=[CH:9][C:8]=1[O:39][CH3:40])=[O:5].[C:46](O)(=O)[CH3:47]>>[CH3:40][O:39][C:8]1[CH:9]=[C:10]([CH:37]=[CH:38][C:7]=1[NH:6][C:4]([C:3]1[C:2]2[N:1]=[C:46]([CH3:47])[NH:45][C:44]=2[CH:43]=[CH:42][CH:41]=1)=[O:5])[C:11]([N:13]([CH3:36])[C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1)=[O:28])=[O:12]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 183547944-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Product 1

HCID 18355064HCID 18355064, compound

Procedure

A suspension of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (100 mg) in acetic acid (1 ml) was refluxed for 8 hours. After being evaporated in vacuo, the residue was dissolved chloroform and the solution was washed with water and saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)carbonylamino-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (84 mg) as a powder.

Workup

  1. temperaturewas refluxed for 8 hours
  2. customAfter being evaporated in vacuo
  3. dissolutionthe residue was dissolved chloroform
  4. washthe solution was washed with water and saturated aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1)

Sources & evidence

ORD record
ord-b617812748404fd1b98a9d78cbcc079a
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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