HCID 66890101, compound → HCID 178468533, compound

HRID 1897963Notes

Reaction equation

HRID 1897963 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([NH:15][C:16]2[N:20]([C:21]([CH3:24])([CH3:23])[CH3:22])[N:19]=[CH:18][CH:17]=2)[N:12]=[C:11]([CH2:25][C:26]2([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[CH:10]=1)C1C=CC=CC=1>O1CCCC1.CO.[OH-].[OH-].[Pd+2]>[C:21]([N:20]1[C:16]([NH:15][C:13]2[N:12]=[C:11]([CH2:25][C:26]3([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:28][CH2:27]3)[CH:10]=[C:9]([OH:8])[CH:14]=2)=[CH:17][CH:18]=[N:19]1)([CH3:22])([CH3:23])[CH3:24]

Participants

5

Reactant 1

HCID 66890101HCID 66890101, compound

Product 1

HCID 178468533HCID 178468533, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g of 1-tert-butyl 4-ethyl 4-((4-(benzyloxy)-6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)piperidine-1,4-dicarboxylate in 10 ml of tetrahydrofuran and 10 ml of methanol was added 300 mg of 20% palladium hydroxide on carbon, followed by stirring the reaction mixture at room temperature for 2 hours 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-61e9463191d44f4f9600271dbc724f7b
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

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