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Ethanol → 1-allyl-7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 586952
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인쇄 미리보기

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HRID 586952 반응식
C(O)C.[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16](Br)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH3:36])[CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:24][CH:23]=2)=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6].B([O-])([O-])O[C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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.O>[CH2:4]([N:7]1[C:13]2[CH:14]=[CH:15][C:16]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:41][CH:40]=3)=[CH:17][C:12]=2[CH:11]=[C:10]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]([CH3:36])[CH:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:24][CH:23]=2)=[O:20])[CH2:9][CH2:8]1)[CH:5]=[CH2:6]
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참가 물질

8

반응물 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223290481-allyl-7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamideHCID 867568154-Butoxyethoxyphenyl borate

생성물 1

HCID 99607531-allyl-7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide
수율 14.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

In toluene (15 ml), ethanol (1.5 ml) and water (1.5 ml) were suspended 1-allyl-7-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (262 mg), 4-butoxyethoxyphenyl borate (169 mg) and potassium carbonate (196 mg), and the suspension was stirred under argon atmosphere for 30 minutes. Then, to the mixture was added tetrakistriphenylphosphinepalladium (45 mg), and the mixture was heated under argon atmosphere at 100° C. for 6 hours. After allowing to cool, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was separated and purified with silica gel column chromatography (methanol:ethyl acetate=1:16), which was recrystallized from hexane-ethyl acetate to give 1-allyl-7-(4-butoxyethoxyphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 50) (46 mg) as yellow crystals.

후처리

  1. temperatureto cool
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was separated
  7. custompurified with silica gel column chromatography (methanol:ethyl acetate=1:16), which
  8. customwas recrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-8c6341931f05486e981503389c9d3ace
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06936602B1

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