HCID 86619141, compound → HCID 68687399, compound

HRID 2238660Notes

Reaction equation

HRID 2238660 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([CH:29]([F:31])[F:30])[C:23]4=[N:22][CH:21]=3)[C:17]([C:32]#[N:33])=[CH:16][N:15]=2)[CH3:12])[CH:8]=[CH:9][CH:10]=1)=[N+]=[N-].[H][H]>C(O)C.[C].[Pd]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([CH:29]([F:30])[F:31])[C:23]4=[N:22][CH:21]=3)[C:17]([C:32]#[N:33])=[CH:16][N:15]=2)[CH3:12])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 86619141HCID 86619141, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68687399HCID 68687399, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

87 mg of the 2-({1-[3-(azidomethyl)phenyl)ethyl}amino)-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-5-carbonitrile [102-1] was dissolved in 3 mL of ethanol, then 50 mg of 10% palladiumcarbon catalyst was added, and stirred overnight at room temperature in a hydrogen atmosphere. The insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and 76 mg of 2-({1-[3-(aminomethyl)phenyl)ethyl}amino)-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-5-carbonitrile [102-2] was obtained as a yellow solid.

Workup

  1. filtrationThe insolubles were filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-511f82c1f71e471fa19fddb34ed3fd83
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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