HCID 70570435, compound → HCID 68106724, compound

HRID 2403595Notes

Reaction equation

HRID 2403595 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[N:38]=[CH:37][C:36](/[CH:39]=[CH:40]/[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:35][C:34]=4[CH3:46])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([N:12]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:33]4[N:38]=[CH:37][C:36]([CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:35][C:34]=4[CH3:46])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:13])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 70570435HCID 70570435, compound

Product 1

HCID 68106724HCID 68106724, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl (2E)-3-[6-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)-5-methylpyridin-3-yl]acrylate (250 mg) was dissolved in EtOH (4 ml), and 10% Pd/C (80 mg) was added thereto under a hydrogen atmosphere at 1 atm, followed by stirring at room temperature overnight. The mixture was filtrated using Celite as a filtration assistant to remove the catalyst, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain ethyl 3-[6-(4-{5-[3-({[N-(tert-butoxycarbonyl)glycyl](methyl)amino}methyl)phenyl]pyrimidin-2-yl}piperazin-1-yl)-5-methylpyridin-3-yl]propanoate (163 mg).

Workup

  1. filtrationThe mixture was filtrated
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-dd1536a4280d496fb08d53b7e5f0a4ff
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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