Trimethylsilylmethyl Azide → 2-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}thiophene-3-carboxamide

HRID 386144

Reaktionsgleichung

Reaktionsgleichung von HRID 386144
[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:10]=2)=[C:5]([C:22]([NH2:24])=[O:23])[CH:4]=1)#[CH:2].[CH3:25][Si:26]([CH2:29][N:30]=[N+:31]=[N-:32])([CH3:28])[CH3:27].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CN(C=O)C.O>[N:16]1([CH2:15][C:11]2[N:10]=[C:9]([NH:8][C:6]3[S:7][C:3]([C:1]4[N:32]=[N:31][N:30]([CH2:29][Si:26]([CH3:28])([CH3:27])[CH3:25])[CH:2]=4)=[CH:4][C:5]=3[C:22]([NH2:24])=[O:23])[CH:14]=[CH:13][CH:12]=2)[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

Komponenten

6

Edukt 3

HCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 595262705-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

Produkt 1

HCID 595255682-{[6-(Morpholin-4-ylmethyl)pyridin-2-yl]amino}-5-{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}thiophene-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Ethynyl-2-{[6-(morpholin-4-ylmethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 599, Step 4) (75 mg, 0.22 mmol) and trimethylsilylmethyl azide (0.65 ml, 0.44 mmol) were combined in DMF (1.0 mL). CuSO4.5H2O (5.5 mg, 0.022 mmol) in water (0.2 mL) and sodium ascorbate (17 mg, 0.088 mmol) in water (0.2 ml) were added, and the reaction mixture was stirred at room temperature overnight. The reaction was evaporated to dryness, combined with MeOH and silica gel, and evaporated. Flash chromatography (dry load, 0-10% MeOH/EtOAc) afforded the title compound a yellow solid.

Aufarbeitung

  1. customThe reaction was evaporated to dryness
  2. customevaporated
  3. dry with materialFlash chromatography (dry load, 0-10% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-6bf400ae7021417bbf58c81af268be9e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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