(R)-1-Boc-piperidine-3-carboxylic acid hydrazide → HCID 178451955, Verbindung

HRID 1465698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465698
Cl.[Br:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](=[NH:16])OCC)[CH:10]=2)[NH:5][N:4]=1.[NH:17]([C:19]([C@@H:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1)=O)[NH2:18]>CO>[Br:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]3[N:16]=[C:19]([C@@H:21]4[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]4)[NH:17][N:18]=3)[CH:10]=2)[NH:5][N:4]=1

Komponenten

4

Edukt 2

HCID 29922274(R)-1-Boc-piperidine-3-carboxylic acid hydrazideHCID 178468222HCID 178468222, Verbindung

Produkt 1

HCID 178451955HCID 178451955, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Mixture of ethyl 3-bromo-1H-indazole-5-carbimidate hydrochloride (4.1 g, 13.5 mmol) and (R)-tert-butyl 3-(hydrazinecarbonyl)piperidine-1-carboxylate (5.1 g, 20 mmol) in MeOH (25 ml) was heated in a sealed tube at 85° C. overnight. After solvent was evaporated, the residue was diluted with DCM (200 ml) and washed with H2O (50 ml), Dried over Na2SO4; filtered and evaporated solvent. Chromatographed residue eluting with 5% MeOH/DCM to yield (R)-tert-butyl 3-(3-(3-bromo-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate as a white solid (6 g).

Aufarbeitung

  1. customAfter solvent was evaporated
  2. additionthe residue was diluted with DCM (200 ml)
  3. washwashed with H2O (50 ml)
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. customevaporated solvent
  7. washChromatographed residue eluting with 5% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-f00ab3c41a09404ba85886140ca3c237
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999966B2

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