Cesium fluoride → 7-methoxy-4-((6-(1-methyl-1H-1,2,3-triazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline

HRID 1513650

Reaktionsgleichung

Reaktionsgleichung von HRID 1513650
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([CH2:12][O:13][C:14]3[C:23]4[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=4)[N:17]=[CH:16][CH:15]=3)=[N:10][N:11]=2)[CH:8]=1)#[CH:2].C[Si]([CH2:30][N:31]=[N+:32]=[N-:33])(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[F-].[Cs+]>C1COCC1.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:25][O:24][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([O:13][CH2:12][C:9]3[N:7]4[CH:8]=[C:3]([C:1]5[N:33]=[N:32][N:31]([CH3:30])[CH:2]=5)[CH:4]=[CH:5][C:6]4=[N:11][N:10]=3)=[CH:15][CH:16]=[N:17]2)=[CH:22][CH:21]=1

Komponenten

8

Edukt 4

HCID 25953Cesium fluorideHCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 866302634-((6-Ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline

Produkt 1

HCID 576911037-methoxy-4-((6-(1-methyl-1H-1,2,3-triazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-((6-ethynyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)-7-methoxyquinoline (0.200 g, 0.605 mmol), trimethylsilylmethyl azide (0.156 g, 1.21 mmol), sodium ascorbate (0.240 g, 1.21 mmol) in THF (4 mL) and water (1 mL) was added 1 drop of a copper sulfate (0.00966 g, 0.0605 mmol) solution. Stirred for 1 h. Concentrated. Suspended in water and extracted with CH2Cl2 (3×5 mL). Dried over sodium sulfate and concentrated. Took up crude mixture in DMF (4 mL). Added cesium fluoride (0.368 g, 2.42 mmol) and heated to 60° for 1 h. Concentrated. Purified on RPHPLC. Fractions containing product were treated with 9% sodium carbonate and volatiles were removed in vacuo. Product crashed out of solution and was isolated by filtration. MS m/z=388.1 [M+1]+. Calc'd for C20H17N7O2: 387.4.

Aufarbeitung

  1. concentrationConcentrated
  2. extractionextracted with CH2Cl2 (3×5 mL)
  3. dry with materialDried over sodium sulfate
  4. concentrationconcentrated
  5. concentrationConcentrated
  6. customPurified on RPHPLC
  7. additionFractions containing product
  8. additionwere treated with 9% sodium carbonate and volatiles
  9. customwere removed in vacuo
  10. customwas isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-7bcfea5e1e034aacaf761ce657523681
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217177B2

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