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

HRID 429631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 429631
[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].[CH:46](OC)(OC)OC>>[NH:45]1[C:44]2[CH:43]=[CH:42][CH:41]=[C:3]([C:4]([NH:6][C:7]3[CH:38]=[CH:37][C:10]([C:11]([N:13]([CH3:36])[C:14]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=4[O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([N:29]4[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]4)=[O:28])=[O:12])=[CH:9][C:8]=3[O:39][CH3:40])=[O:5])[C:2]=2[N:1]=[CH:46]1

Komponenten

3

Edukt 2

HCID 9005Trimethyl orthoformateHCID 183547944-(2,3-diaminophenyl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Produkt 1

HCID 183548084-(1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

Versuchsvorschrift

A mixture of 4-(2,3-diaminobenzoyl)amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (90 mg) and trimethyl orthoformate (1 ml) was refluxed for 4 hours. After removing excess reagent by evaporation, the residue was dissolved in 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 4-(1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide (51 mg) as a powder.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a040008e19be42e3a4336e29670ac81c
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316482B1

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