tert-butyl 4-((2-((benzyloxy)carbonyl)hydrazino)carbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1-carboxylate → tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(hydrazinocarbonyl)piperidine-1-carboxylate

HRID 1897958Notes

Reaction equation

HRID 1897958 reaction equation
C(OC([NH:11][NH:12][C:13]([C:15]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:36]3[N:40]([C:41]([CH3:44])([CH3:43])[CH3:42])[N:39]=[CH:38][CH:37]=3)[N:30]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:14])=O)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[C:41]([N:40]1[C:36]([NH:35][C:31]2[N:30]=[C:29]([CH2:28][C:15]3([C:13]([NH:12][NH2:11])=[O:14])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:17][CH2:16]3)[CH:34]=[CH:33][CH:32]=2)=[CH:37][CH:38]=[N:39]1)([CH3:42])([CH3:43])[CH3:44]

Participants

4

Reactant 1

HCID 66889476tert-butyl 4-((2-((benzyloxy)carbonyl)hydrazino)carbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 66889292tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(hydrazinocarbonyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 535 mg of tert-butyl 4-((2-((benzyloxy)carbonyl)hydrazino)carbonyl)-4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1-carboxylate in 10 ml of methanol was added 200 mg of 20% palladium hydroxide on carbon, followed by stirring the reaction mixture at room temperature overnight under hydrogen atmosphere. Palladium catalyst was filtered off using Celite, washed with methanol, and the filtrate was concentrated in vacuo to give the title compound as a pale brown solid.

Workup

  1. filtrationPalladium catalyst was filtered off
  2. washwashed with methanol
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1f931e32a09447a5b05d51fe74c48b04
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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