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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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(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 1432031
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HRID 1432031 반응식
[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
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참가 물질

8

반응물 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

생성물 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

시약·촉매·용매 5

HCID 24463Copper sulfate pentahydrate
촉매
HCID 962Water용매
HCID 6386tert-Butanol용매
HCID 8857Ethyl Acetate용매
HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-949266f651674085b684b71ffcb34ae8
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612060B2

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