HCID 67385909, compound → HCID 67386141, compound

HRID 906009Notes

Reaction equation

HRID 906009 reaction equation
C(OC([N:11]1[CH2:16][C@H:15]([NH:17][C:18]([NH:20][C:21]2[N:22]=[C:23]3[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:24]3=[N:25][CH:26]=2)=[O:19])[CH2:14][C@@H:13]([CH3:38])[CH2:12]1)=O)C1C=CC=CC=1>CCO.[OH-].[Pd+2].[OH-]>[CH3:38][C@H:13]1[CH2:12][NH:11][CH2:16][C@H:15]([NH:17][C:18]([NH:20][C:21]2[N:22]=[C:23]3[CH:29]=[CH:28][N:27]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:35])([CH3:37])[CH3:36])[C:24]3=[N:25][CH:26]=2)=[O:19])[CH2:14]1

Participants

4

Reactant 1

HCID 67385909HCID 67385909, compound

Product 1

HCID 67386141HCID 67386141, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3R,5R)-3-methyl-5-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureido}-piperidine-1-carboxylic acid benzyl ester (1.04 g, 1.93 mmol) and palladium hydroxide 20% on carbon (0.15 g) in 20 mL of EtOH was stirred at RT under hydrogen (1 atm) for 2 hours before being filtered. The dark brown filtrate was evaporated to give 0.76 g of 1-((3R,5R)-5-methyl-piperidin-3-yl)-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-urea (>95%).

Workup

  1. filtrationbefore being filtered
  2. customThe dark brown filtrate was evaporated

Sources & evidence

ORD record
ord-9622ac0db3b64b72a68cb8880ad4539e
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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