HCID 46896668, compound → HCID 66616560, compound

HRID 1046535Notes

Reaction equation

HRID 1046535 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[N:23]4[CH:24]=[CH:25][CH:26]=[C:27]([O:28]CC5C=CC=CC=5)[C:22]4=[N:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][CH:9]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[N:23]4[CH:24]=[CH:25][CH:26]=[C:27]([OH:28])[C:22]4=[N:21][CH:20]=3)[CH:16]=[CH:15][N:14]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 46896668HCID 46896668, compound

Product 1

HCID 66616560HCID 66616560, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[4-(8-benzyloxy-imidazo[1,2-a]pyridine-3-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (0.215 g) and Pd/C (10%, 600 mg) in EtOH (200 mL) was stirred under H2 overnight. The reaction mixture was heated and filtered hot through silica. The product was washed with DCM, and the filtrate concentrated and dried to provide 4-[4-(8-hydroxy-imidazo[1,2-a]pyridine-3-yl)-pyrimidin-2-ylamino]-cyclohexanecarboxylic acid ethyl ester (128 mg), which was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationfiltered hot through silica
  3. washThe product was washed with DCM
  4. concentrationthe filtrate concentrated
  5. customdried

Sources & evidence

ORD record
ord-cd05a2c3780043d3b85a5f8c3a3f8806
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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