4-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester → 4-[3-(3-Amino-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 45818Notes

Reaction equation

HRID 45818 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([N+:31]([O-])=O)[CH:26]=3)=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:16]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=3)=[N:15]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 671840714-[3-(3-Nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 671844154-[3-(3-Amino-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To crude 4-[3-(3-nitro-phenyl)-4-pyridin-4-yl-pyrazol-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.75 mmol) in methanol (20 mL) Pd/C 10% (190 mg) was added. The reaction was stirred under hydrogen atmosphere (45 psi) at room temperature for six hours. The suspension was filtered to remove the catalyst, and then concentrated to give the crude product that was used in the next step without further purification.

Workup

  1. filtrationThe suspension was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3312b01a7ffd485e9ae00a5e8e131fe2
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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