HCID 68686560, compound → HCID 68688595, compound

HRID 2238661Notes

Reaction equation

HRID 2238661 reaction equation
[F:1][CH:2]([F:32])[C:3]1[C:4]2[N:5]([C:9]([C:12]3[C:17]([C:18]#[N:19])=[CH:16][N:15]=[C:14]([NH:20][C@H:21]([C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=4)[CH3:22])[N:13]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.[H][H]>C(O)C.O1CCCC1.[C].[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([C@@H:21]([NH:20][C:14]2[N:13]=[C:12]([C:9]3[N:5]4[CH:6]=[CH:7][CH:8]=[C:3]([CH:2]([F:32])[F:1])[C:4]4=[N:11][CH:10]=3)[C:17]([C:18]#[N:19])=[CH:16][N:15]=2)[CH3:22])=[CH:24][CH:25]=1

Participants

6

Reactant 2

HCID 68686560HCID 68686560, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68688595HCID 68688595, compoundYield 18.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

83 mg of the 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-{[(1S)-1-(4-nitrophenyl)ethyl]amino}pyrimidine-5-carbonitrile [103-1] was dissolved in a mixture solvent of 2 mL of ethanol and 3 mL of tetrahydrofuran, then 40 mg of 10% palladiumcarbon catalyst was added, and stirred overnight at room temperature in a hydrogen atmosphere. The insolubles were filtered through celite and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by preparative thin-layer chromatography, and 14 mg of 2-{[(1S)-1-(4-aminophenyl)ethyl]amino}-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-5-carbonitrile [103-2] was obtained as pale yellow amorphous.

Workup

  1. filtrationThe insolubles were filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto obtain a residue
  4. customThe residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-b35a96a3d855460e8d115b8b2be381b6
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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