(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 1432025Notes

Reaction equation

HRID 1432025 reaction equation
[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]

Participants

8

Reactant 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

Product 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

Reagents, catalysts & solvents 5

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ca5194fcb9cb4df4a739b162ada00146
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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