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Imidazole → Tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate

HRID 595513
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595513
[Cl:1][C:2]1[CH:24]=[C:23]([NH:25][CH:26]([CH3:28])[CH3:27])[C:5]([C:6]([NH:8][NH:9][C:10](=[O:22])[CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][OH:13])=[O:7])=[CH:4][N:3]=1.N1C=CN=C1.[C:34]([Si:38](Cl)([CH3:40])[CH3:39])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl>[Si:38]([O:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:18])[CH3:19])[C:10]([NH:9][NH:8][C:6](=[O:7])[C:5]1[C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[CH:24][C:2]([Cl:1])=[N:3][CH:4]=1)=[O:22])([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:40])[CH3:39]
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Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 131732603Tert-butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate

Produkt 1

HCID 131732604Tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

tert-Butyl (1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-3-hydroxy-1-oxopropan-2-yl)carbamate (53) (1 g, 2 mmol) in DCM (10 mL), imidazole (7 mmol, 3 equiv.) was added and stirred at room temperature for 10 min. Reaction mixture was cooled to 0° C., t-butyl dimethyl silyl chloride (3.6 mmol, 1.5 equiv.) was added in portions and stirred the reaction mixture overnight at room temperature. Diluted the reaction mixture using DCM, the DCM layer was washed with water. The organic layer was collected, dried over Na2SO4, filtered and concentrated to get tert-butyl (3-((tert-butyldimethylsilyl)oxy)-1-(2-(6-chloro-4-(isopropylamino)nicotinoyl)hydrazinyl)-1-oxopropan-2-yl)carbamate (54). LC/MS: Purospher@star RP-18, 4×55 mm, 3 μm; Solvent A=10% ACN: 90% H2O: 20 mM NH4OAc; Solvent B=90% ACN: 10% H2O: 20 mM NH4COOAc; gradient 0-100% B over 1.5 min (3.2 min run time); retention time: 2.319 min; LCMS (ES-API), m/z 530.2 (M+H).

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled to 0° C.
  3. stirringstirred the reaction mixture overnight at room temperature
  4. additionDiluted the reaction mixture
  5. washthe DCM layer was washed with water
  6. customThe organic layer was collected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6fbe87d50517432483401f7f4c5db760
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242976B2

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