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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
ノート
印刷プレビュー

反応式

HRID 1432031 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 5

HCID 24463Copper sulfate pentahydrate触媒
HCID 962Water溶媒
HCID 6386tert-Butanol溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-949266f651674085b684b71ffcb34ae8
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612060B2

反応ノート

読み込み中…

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