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Dimethylformamide → N-methyl-4-{[N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-N-(2-pyridin-3-ylethyl)amino]methyl}benzamide dihydrochloride

HRID 1504187
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1504187
P([C:9]#[N:10])(=O)(OCC)OCC.CN(C=O)C.[CH3:16][N:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]([CH2:42][C:43]3[CH:51]=[CH:50][C:46]([C:47]([OH:49])=O)=[CH:45][CH:44]=3)[CH2:34][CH2:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]1=[O:52].[ClH:53].CN>C(OCC)(=O)C.C(N(CC)CC)C>[ClH:53].[ClH:53].[CH3:9][NH:10][C:47](=[O:49])[C:46]1[CH:50]=[CH:51][C:43]([CH2:42][N:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][C:23]2[CH:22]=[C:21]3[C:26](=[CH:25][CH:24]=2)[N:17]([CH3:16])[C:18](=[O:52])[CH:19]=[CH:20]3)[CH2:34][CH2:35][C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[CH:44][CH:45]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 6364545Methylamine hydrochlorideHCID 70657042HCID 70657042, Verbindung

Produkt 1

HCID 86762684N-methyl-4-{[N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-N-(2-pyridin-3-ylethyl)amino]methyl}benzamide dihydrochlorideAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Diethyl phosphorocyanidate (39.1 mg) was added to a DMF solution (1 ml) of 4-{[N-[5-(1-methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)pentyl]-N-(2-pyridin-3-ylethyl)amino]methyl}benzoic acid (0.10 g), methylamine hydrochloride (27 mg), and triethylamine (0.07 ml), and the mixture was stirred at room temperature overnight. Ice water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water and a saturated sodium chloride aqueous solution, in this order, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1). The purified product was concentrated under reduced pressure. A 1N-hydrogen chloride ethanol solution (0.16 ml) was added to the solution of the residue in ethanol, and stirred for 30 minutes at room temperature. The precipitated insoluble matter was collected by filtration, washed with ethyl acetate, and dried to give the title compound (81.3 mg) as a white powder.

Aufarbeitung

  1. washThe organic layer was washed with water
  2. dry with materiala saturated sodium chloride aqueous solution, in this order, then dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)
  5. concentrationThe purified product was concentrated under reduced pressure
  6. additionA 1N-hydrogen chloride ethanol solution (0.16 ml) was added to the solution of the residue in ethanol
  7. stirringstirred for 30 minutes at room temperature
  8. filtrationThe precipitated insoluble matter was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4cd33d6ba4fa49fbafc716327e9ea064
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09212187B2

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