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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 429635
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 429635
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-3H-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-1H-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-f1e246ceb6874a92aecf44994c375f54
Quelldatensatz
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06316482B1

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