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Water → 7-[4-(2-butoxyethoxy)phenyl]-1-(2-ethoxyethyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide

HRID 587050
ノート
印刷プレビュー

反応式

HRID 587050 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[CH2:10][CH2:9][C:8]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:34])[CH:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:22][CH:21]=3)=[O:18])=[CH:7][C:6]=2[CH:35]=1.B([O-])([O-])O[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][CH2:50][CH3:51])=[CH:40][CH:39]=1.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.C(O)C.O.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>[CH2:48]([O:47][CH2:46][CH2:45][O:44][C:41]1[CH:40]=[CH:39][C:38]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[CH2:10][CH2:9][C:8]([C:17]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([CH2:26][N:27]([CH3:34])[CH:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)=[CH:24][CH:25]=4)=[O:18])=[CH:7][C:6]=3[CH:35]=2)=[CH:43][CH:42]=1)[CH2:49][CH2:50][CH3:51]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22328889HCID 22328889、化合物HCID 867568154-Butoxyethoxyphenyl borate

生成物 1

HCID 223290917-[4-(2-butoxyethoxy)phenyl]-1-(2-ethoxyethyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide収率 3.9%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 86587398Ethanol toluene water溶媒

実験手順

In toluene/ethanol/water (=20/1/1, 14.3 ml) was dissolved 7-bromo-1-(2-ethoxyethyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (0.32 g). To the solution were added 4-(2-butoxyethoxy)phenyl borate (0.17 g) and potassium carbonate (0.18 g), and the mixture was stirred for 30 minutes under argon atmosphere. To the mixture was added tetrakistriphenylphosphinepalladium (27 mg), and the mixture was heated to reflux for 14 hours. After cooled to room temperature, the reaction solution was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1). The purified residue was dissolved in ethyl acetate, which was filtered to give a solution. The solvent was removed under reduced pressure, which was recrystallized from isopropyl ether/ethyl acetate to give 7-[4-(2-butoxyethoxy)phenyl]-1-(2-ethoxyethyl)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide (Compound 90) (15 mg).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 14 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was purified with silica gel column chromatography (ethyl acetate/ethanol=3/1)
  8. dissolutionThe purified residue was dissolved in ethyl acetate
  9. filtrationwhich was filtered
  10. customto give a solution
  11. customThe solvent was removed under reduced pressure, which
  12. customwas recrystallized from isopropyl ether/ethyl acetate

出典と根拠

ORDレコード
ord-f30db880102f47b5b0fcd10841ec77f4
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06936602B1

反応ノート

読み込み中…

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