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

HRID 1465698Notes

Reaction equation

HRID 1465698 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 178451955HCID 178451955, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f00ab3c41a09404ba85886140ca3c237
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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