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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 1533762
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1533762
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 284Formic AcidHCID 18354861HCID 18354861, Verbindung

Produkt 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]benzamideAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-144662d5b2d84d8e8eae5b54dd3ba0c8
Quelldatensatz
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06207693B1

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