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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 69016
Notes
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Reaction equation

HRID 69016 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 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 dihydrochlorideYield 69.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0612f67e148546fba1d335d9df2b981f
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822453B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes