Formic Acid → 3-methoxy-4-(2-methoxymethyl-1H-benzimidazol-4-yl)carbonylamino-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 1533762Notes

Reaction equation

HRID 1533762 reaction equation
C([N:8]1[C:12]2[C:13]([C:17]([NH:19][C:20]3[CH:51]=[CH:50][C:23]([C:24]([N:26]([CH3:49])[C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=4[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]4)=[O:41])=[O:25])=[CH:22][C:21]=3[O:52][CH3:53])=[O:18])=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:54][O:55][CH3:56])C1C=CC=CC=1.C(O)=O>CO>[CH3:53][O:52][C:21]1[CH:22]=[C:23]([CH:50]=[CH:51][C:20]=1[NH:19][C:17]([C:13]1[C:12]2[N:8]=[C:9]([CH2:54][O:55][CH3:56])[NH:10][C:11]=2[CH:16]=[CH:15][CH:14]=1)=[O:18])[C:24]([N:26]([CH3:49])[C:27]1[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][C:28]=1[O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([N:42]1[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]1)=[O:41])=[O:25]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 18354861HCID 18354861, compound

Product 1

HCID 183551013-methoxy-4-(2-methoxymethyl-1H-benzimidazol-4-yl)carbonylamino-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideYield 27.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(3-benzyl-2-methoxymethyl-3 H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]-phenyl]benzamide (200 mg) and 5% formic acid in methanol solution (10 ml) was refluxed for 24 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved in chloroform. The solution was washed with saturated aqueous sodium bicarbonate solution and the organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by preparative thin-layer chromatography (chloroform-methanol=10:1) to give 3-methoxy-4-(2-methoxymethyl-1 H-benzimidazol-4-yl)carbonylamino-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (48 mg) as a powder.

Workup

  1. temperaturewas refluxed for 24 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe solution was washed with 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-144662d5b2d84d8e8eae5b54dd3ba0c8
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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