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Potassium Carbonate → 7-(4-ethoxyphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]2,3-dihydro-1-benzoazepine-4-carboxamide

HRID 1387987
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Reaktionsgleichung

Reaktionsgleichung von HRID 1387987
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH3:11])=[CH:5][CH:4]=1.Br[C:15]1[CH:16]=[CH:17][C:18]2[N:24]([CH3:25])[CH2:23][CH2:22][C:21]([C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([CH2:35][N:36]([CH3:43])[CH:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[CH:31][CH:30]=3)=[O:27])=[CH:20][C:19]=2[CH:44]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH3:25])[CH2:23][CH2:22][C:21]([C:26]([NH:28][C:29]4[CH:30]=[CH:31][C:32]([CH2:35][N:36]([CH3:43])[CH:37]5[CH2:42][CH2:41][O:40][CH2:39][CH2:38]5)=[CH:33][CH:34]=4)=[O:27])=[CH:20][C:19]=3[CH:44]=2)=[CH:4][CH:5]=1)[CH3:11]
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Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 223290367-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamideHCID 86756168HCID 86756168, Verbindung

Produkt 1

HCID 184725957-(4-ethoxyphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]2,3-dihydro-1-benzoazepine-4-carboxamideAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 8857Ethyl AcetateLösungsmittelHCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

In water:ethanol:toluene (1:1:10, 18.0 ml) were dissolved 4-ethoxyphenyl borate (252 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]-methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (613 mg), and to the mixture was added potassium carbonate (420 mg). The mixture was stirred under argon atmosphere for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (59 mg). Under argon atmosphere, the mixture was refluxed for 17 hours. The mixture was diluted with ethyl acetate (200 ml) and washed with water (50 ml) and saturated brine (50 ml). The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1) and recrystallized from ethanol to give 7-(4-ethoxyphenyl)-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide (Compound 306) (230 mg, 35%).

Aufarbeitung

  1. temperatureUnder argon atmosphere, the mixture was refluxed for 17 hours
  2. washwashed with water (50 ml) and saturated brine (50 ml)
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (75 g, ethyl acetate:ethanol=9:1)
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a013a5de37e8407cbb6dfa5d031387e7
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06268354B1

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