(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 1432025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432025
[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]

Komponenten

8

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24463Copper sulfate pentahydrateKatalysatorHCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ca5194fcb9cb4df4a739b162ada00146
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612060B2

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