HCID 67314324, compound → HCID 67313969, compound

HRID 1010902Notes

Reaction equation

HRID 1010902 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([C:19]2[CH:24]=[CH:23][C:22]([C@@H:25]([NH:27][C:28]3[N:33]=[C:32]([C:34]4[N:38]5[CH:39]=[CH:40][CH:41]=[C:42]([CH2:43][CH3:44])[C:37]5=[N:36][CH:35]=4)[C:31]([C:45]#[N:46])=[CH:30][N:29]=3)[CH3:26])=[CH:21][CH:20]=2)[OH:18])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH2:43]([C:42]1[C:37]2[N:38]([C:34]([C:32]3[C:31]([C:45]#[N:46])=[CH:30][N:29]=[C:28]([NH:27][C@H:25]([C:22]4[CH:21]=[CH:20][C:19]([CH:17]([OH:18])[CH:14]5[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]5)=[CH:24][CH:23]=4)[CH3:26])[N:33]=3)=[CH:35][N:36]=2)[CH:39]=[CH:40][CH:41]=1)[CH3:44]

Participants

4

Reactant 1

HCID 67314324HCID 67314324, compound

Product 1

HCID 67313969HCID 67313969, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

118 mg of the compound [25-2] was dissolved in 4 mL of ethanol, then 50 mg of a carbon catalyst of 20% palladium hydroxide was added thereto, and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The catalyst was filtered through celite, the filtrate was concentrated under reduced pressure, and then the resulting residue was purified by preparative thin-layer chromatography, to obtain 66 mg of 4-(8-ethylimidazo[1,2-a]pyridin-3-yl)-2-[((1S)-1-{4-[hydroxy(piperidin-4-yl)methyl]phenyl}ethyl)amino]pyrimidine-5-carbonitrile [25-3] (hereinafter, referred to as the compound [25-3]).

Workup

  1. filtrationThe catalyst was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-320f806d193743b391383f63318e8aa8
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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