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Cesium carbonate → 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine

HRID 1017637
ノート
印刷プレビュー

反応式

HRID 1017637 の反応式
[C:1]1([N:7]2[C:11]3[NH:12][C:13](=[O:20])[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:15][C:10]=3[N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:22][N:23]1[C:27]([CH2:28]Cl)=[N:26][CH:25]=[N:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:18][C:16]([C:14]1[CH:15]=[C:10]2[N:9]=[N:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:11]2=[N:12][C:13]=1[O:20][CH2:28][C:27]1[N:23]([CH3:22])[N:24]=[CH:25][N:26]=1)([CH3:17])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochlorideHCID 1358341243-Phenyl-6-(tert-butyl)-3,4-dihydro-1,2,3-triazolo[4,5-b]pyridin-5-one

生成物 1

HCID 98204146-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine収率 83%

試薬・触媒・溶媒 3

HCID 311
Citric Acid
溶媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-phenyl-6-(tert-butyl)-3,4-dihydro-1,2,3-triazolo[4,5-b]pyridin-5-one (0.025 g, 0.093 g), 2-methyl-3-chloromethyl-1,2,4-triazole hydrochloride (0.15 g, 1.1 mmol) and cesium carbonate (0.65 g, 2.0 mmol) in dry DMF (4 ml) was stirred at r.t. for 20 h. The mixture was diluted with water (50 ml) and 1M citric acid (5 ml), and extracted with dichloromethane (2×25 ml). The extracts were dried (Na2SO4), filtered and concentrated. Preparative thin-layer chromatography, eluting with 5% methanol-dichloromethane, gave 6-(1,1-dimethylethyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-3-phenyl-1,2,3-triazolo[4,5-b]pyridine (0.028 g, 83%) as a white solid, m.p. 165-167° C. δH (360 MHz; CDCl3) 1.43 (9H, s), 3.94 (3H, s), 5.69 (2H, s), 7.46 (1H, t, J=7), 7.60 (2H, dd, J=7 and 7), 7.93 (1H, s), 8.20 (2H, d, J=7) and 8.31 (1H, s); m/z (ES+) 364 (M+H+).

後処理

  1. extractionextracted with dichloromethane (2×25 ml)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washPreparative thin-layer chromatography, eluting with 5% methanol-dichloromethane

出典と根拠

ORDレコード
ord-6f053d8340df402193106a5f7144975d
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06479506B1

反応ノート

読み込み中…

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