Sodium Iodide → 7-[4-(2-butoxyethoxy)phenyl]-1-(2-oxopropyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

HRID 587080

반응식

HRID 587080 반응식
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26]4([CH3:31])OCC[O:27]4)[CH2:23][CH2:22][C:21]([C:32]([NH:34][C:35]4[CH:40]=[CH:39][C:38]([CH2:41][N:42]([CH3:49])[CH:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)=[CH:37][CH:36]=4)=[O:33])=[CH:20][C:19]=3[CH:50]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[I-].[Na+].C(#N)C>O>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([CH2:25][C:26](=[O:27])[CH3:31])[CH2:23][CH2:22][C:21]([C:32]([NH:34][C:35]4[CH:36]=[CH:37][C:38]([CH2:41][N:42]([CH3:49])[CH:43]5[CH2:48][CH2:47][O:46][CH2:45][CH2:44]5)=[CH:39][CH:40]=4)=[O:33])=[CH:20][C:19]=3[CH:50]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 21585214Cerium trichloride heptahydrateHCID 223292047-[4-(2-butoxyethoxy)phenyl]-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide

생성물 1

HCID 223292497-[4-(2-butoxyethoxy)phenyl]-1-(2-oxopropyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide수율 55.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of 7-[4-(2-butoxyethoxy)phenyl]-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (100 mg), cerium chloride heptahydrate (300 mg), sodium iodide (19 mg) and acetonitrile (5 ml) was stirred at 60° C. for 5 days. Water was added to the reaction system, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethanol:ethyl acetate=1:3) to give 7-[4-(2-butoxyethoxy)phenyl]-1-(2-oxopropyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (Compound 108) (52 mg) as yellow crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was separated
  6. custompurified with column chromatography (ethanol:ethyl acetate=1:3)

출처 및 근거

ORD 기록
ord-14c22032a794412aaf33bd3ab4744245
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936602B1

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