HCID 178452121, compound → HCID 178452119, compound

HRID 20302

Reaction equation

HRID 20302 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([N+:22]([O-])=O)=[CH:20][NH:19][N:18]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.CN(C=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([NH2:22])=[CH:20][NH:19][N:18]=2)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178452121HCID 178452121, compound

Product 1

HCID 178452119HCID 178452119, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

4-[(4-Nitro-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (13.05 g) was dissolved in ethanol/DMF (300 ml/75 ml), treated with 10% palladium on carbon (500 mg) then hydrogenated at room temperature and pressure overnight. The catalyst was removed by filtration through Celite and the filtrate evaporated and re-evaporated with toluene. The crude material was purified by flash column chromatography eluting with EtOAc then 2% MeOH/EtOAc then 5% MeOH/EtOAc. Product containing fractions were combined and evaporated to give 8.78 g of 4-[(4-amino-1H-pyrazole-3-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a brown foam. (LC/MS: Rt 1.91, [M+H]+ 310).

Workup

  1. customthen hydrogenated at room temperature
  2. custompressure overnight
  3. customThe catalyst was removed by filtration through Celite
  4. customthe filtrate evaporated
  5. customre-evaporated with toluene
  6. customThe crude material was purified by flash column chromatography
  7. washeluting with EtOAc
  8. additionProduct containing fractions
  9. customevaporated

Sources & evidence

ORD record
ord-6ce96a5154a4438bac2f558f0b1ed6a2
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Linked notes

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