(R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine → (R)-2-((1-((R)-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydro-naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)methyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

HRID 1432031Notes

Reaction equation

HRID 1432031 reaction equation
[CH2:1]([C@@H:4]1[C:9](=[O:10])[NH:8][C:7]2[N:11]=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]1[S:15]([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16])[C:2]#[CH:3].[N:25]([C@@H:28]1[CH2:37][CH2:36][CH2:35][C:34]2[CH:33]=[C:32]([CH2:38][N:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[CH:31]=[CH:30][C:29]1=2)=[N+:26]=[N-:27]>O1CCOCC1.CC(O)(C)C.O.CCOC(C)=O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[N:39]1([CH2:38][C:32]2[CH:33]=[C:34]3[C:29](=[CH:30][CH:31]=2)[C@H:28]([N:25]2[CH:3]=[C:2]([CH2:1][C@@H:4]4[C:9](=[O:10])[NH:8][C:7]5[N:11]=[CH:12][CH:13]=[CH:14][C:6]=5[N:5]4[S:15]([C:18]4[CH:19]=[CH:20][C:21]([CH3:22])=[CH:23][CH:24]=4)(=[O:16])=[O:17])[N:27]=[N:26]2)[CH2:37][CH2:36][CH2:35]3)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

8

Reactant 2

HCID 86604857(R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidineHCID 86604881(R)-2-(prop-2-ynyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 11707098(R)-2-((1-((R)-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydro-naphthalen-1-yl)-1H-1,2,3-triazol-4-yl)methyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one

Reagents, catalysts & solvents 5

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

Procedure

To a solution of (R)-2-(prop-2-ynyl)-1-tosyl-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one (210 mg, 0.615 mmol) and (R)-1-((5-azido-5,6,7,8-tetrahydronaphthalen-2-yl)methyl)piperidine (183 mg, 0.677 mmol) in dioxane (3 mL) and t-BuOH (4 mL) was added a solution of copper(2+) sulfate, pentahydrate (43.0 μl, 0.615 mmol) in water (1 mL), followed by a solution of (+)-sodium 1-ascorbate (122 mg, 615 μmol). The resulting solution was stirred at room temperature overnight. The reaction was diluted with EtOAc, washed with brine, dried over Na2SO4, and evaporated to dryness. Flash chromatography (SiO2, EtOAc to EtOAc/2M NH3 in MeOH=100:5 to 100:10 to 100:15) of the residue 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-949266f651674085b684b71ffcb34ae8
Source dataset
uspto-grants-2009_11
Patent number
US07612060B2

Reaction notes

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