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

HRID 587094
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HRID 587094 반응식
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[C:18]1[CH:19]=[CH:20][C:21]2[N:27]([CH2:28][CH2:29][CH3:30])[CH2:26][CH2:25][C:24]([C:31]([NH:33][C:34]3[CH:39]=[CH:38][C:37]([CH2:40][N:41]([CH3:48])[CH:42]4[CH2:47][CH2:46][O:45][CH2:44][CH2:43]4)=[CH:36][CH:35]=3)=[O:32])=[CH:23][C:22]=2[CH:49]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:48][N:41]([CH2:40][C:37]1[CH:36]=[CH:35][C:34]([NH:33][C:31]([C:24]2[CH2:25][CH2:26][N:27]([CH2:28][CH2:29][CH3:30])[C:21]3[CH:20]=[CH:19][C:18]([C:3]4[CH:8]=[CH:7][C:6]([N:9]5[CH2:14][CH2:13][O:12][CH2:11][CH2:10]5)=[CH:5][CH:4]=4)=[CH:49][C:22]=3[CH:23]=2)=[O:32])=[CH:39][CH:38]=1)[CH:42]1[CH2:43][CH2:44][O:45][CH2:46][CH2:47]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 223289007-bromo-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamideHCID 867561794-Morpholinophenyl borate

생성물 1

HCID 22329104N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-1-propyl-2,3-dihydro-1-benzazepine-4-carboxamide수율 48.9%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

실험 절차

4-morpholinophenyl borate (237 mg) and 7-bromo-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (391 mg) were dissolved in water:ethanol toluene (=1:1:10, v/v, 18.0 ml), and potassium carbonate (253 mg) was added thereto. This mixture was stirred at room temperature for 30 minutes under argon atmosphere, tetrakistriphenylphosphinepalladium (35 mg) was added thereto, and the mixture was heated to reflux for 10 hours under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine. 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 (ethyl acetate→ethyl acetate:ethanol=10:1), which was further recrystallized from ethyl acetate-diisopropyl ether-hexane to give N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-7-(4-morpholinophenyl)-1-propyl-2,3-dihydro-1-benzazepine-4-carboxamide (222 mg) as yellow crystals.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 10 hours under argon atmosphere
  3. washwashed with water and saturated brine
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (ethyl acetate→ethyl acetate:ethanol=10:1), which
  7. customwas further recrystallized from ethyl acetate-diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-9f66748f92fc40959c21e7989fd592df
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06936602B1

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