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Benzophenone imine → Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-(benzhydrylideneamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

HRID 2353877
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인쇄 미리보기

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HRID 2353877 반응식
CC(C)([O-])C.[Na+].[C:7](=[NH:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH:21]([O:24][C:25]([N:27]1[CH2:33][CH2:32][CH2:31][CH:30]([N:34]([C:50](=[O:52])[CH3:51])[CH2:35][C:36]2[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=2)[C:29]2[CH:53]=[CH:54][C:55](Br)=[CH:56][C:28]1=2)=[O:26])([CH3:23])[CH3:22]>C1(C)C=CC=CC=1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:50]([N:34]([CH2:35][C:36]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:48])([F:47])[F:49])[CH:37]=1)[CH:30]1[CH2:31][CH2:32][CH2:33][N:27]([C:25]([O:24][CH:21]([CH3:23])[CH3:22])=[O:26])[C:28]2[CH:56]=[C:55]([N:20]=[C:7]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:54]=[CH:53][C:29]1=2)(=[O:52])[CH3:51]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 59003154Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate

생성물 1

HCID 86616066Isopropyl 5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-(benzhydrylideneamino)-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate수율 89%

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 1140Toluene용매
HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

Combine tris(dibenzylideneacetone)dipalladium (0) (0.077 g, 0.084 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphyl (0.157 g, 0.252 mmol) and sodium t-butoxide (0.113 g, 1.18 mmol) in toluene (5 mL) and purge this suspension with nitrogen at room temperature for 5 min. Add benzophenoneimine (0.155 mL, 0.924 mmol) followed by isopropyl-5-[acetyl-(3,5-bistrifluoromethylbenzyl)amino]-8-bromo-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (0.500 g, 0.840 mmol) and heat this mixture at 80° C. under nitrogen for 1 h. Cool the mixture to room temperature, dilute with dichloromethane and filter through Celite. Remove the filtrate solvent under reduced pressure and purify the residue using chromatography on silica gel, eluting with hexanes/ethyl acetate (60:40), to provide the title compound as an orange oil (0.520 g, 89%): APCI MS 696 (M+H).

후처리

  1. temperatureCool the mixture to room temperature
  2. filtrationfilter through Celite
  3. customRemove the filtrate solvent under reduced pressure
  4. custompurify the residue
  5. washeluting with hexanes/ethyl acetate (60:40)

출처 및 근거

ORD 기록
ord-dbc5c494f9044566afbda68b8889ce3e
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07749992B2

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