(R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanone → (R)-4-(3,4-dichlorophenylsulfonyl)-3-((1-((R)-3-(2,2,2-trifluoroacetyl)-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinolin-7-yl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

HRID 1432025노트

반응식

HRID 1432025 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]#[CH:21])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:22]([C@H:25]1[C:38]2[CH:37]=[CH:36][C:35]3[CH2:34][N:33]([C:39](=[O:44])[C:40]([F:43])([F:42])[F:41])[CH2:32][CH2:31][C:30]=3[C:29]=2[CH2:28][CH2:27][CH2:26]1)=[N+:23]=[N-:24]>O1CCOCC1.CC(O)(C)C.O.CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]2[N:24]=[N:23][N:22]([C@H:25]3[C:38]4[CH:37]=[CH:36][C:35]5[CH2:34][N:33]([C:39](=[O:44])[C:40]([F:41])([F:43])[F:42])[CH2:32][CH2:31][C:30]=5[C:29]=4[CH2:28][CH2:27][CH2:26]3)[CH:21]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

8

반응물 2

HCID 58597280(R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanoneHCID 86604867(R)-4-(3,4-dichlorobenzenesulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one

생성물 1

HCID 57932511(R)-4-(3,4-dichlorophenylsulfonyl)-3-((1-((R)-3-(2,2,2-trifluoroacetyl)-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinolin-7-yl)-1H-1,2,3-triazol-4-yl)methyl)-3,4-dihydropyrazin-2(1H)-one

시약·촉매·용매 5

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매2회HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of (R)-4-(3,4-dichlorophenylsulfonyl)-3-(prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one (345 mg, 1 mmol) and (R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanone (324 mg, 1 mmol) in dioxane (3 mL) and t-BuOH (4 mL) was added a solution of copper(2+) sulfate, pentahydrate (249 mg, 1 mmol) in water (0.5 mL), followed by a solution of (+)-sodium 1-ascorbate (198 mg, 1 mmol) in water (0.5 mL). The resulting solution was stirred at room temperature for 16 h. The reaction was diluted with EtOAc, washed with brine, dried over Na2SO4, and evaporated to dryness. Flash chromatography (SiO2, EtOAc/hexane=2:1 to pure EtOAc) afforded the title compound as a white solid.

후처리

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness

출처 및 근거

ORD 기록
ord-ca5194fcb9cb4df4a739b162ada00146
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612060B2

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