Sodium Bicarbonate → HCID 11554545, compound

HRID 2238684Notes

Reaction equation

HRID 2238684 reaction equation
[C:1]([C:4]1[C:5]2[N:6]([C:10]([C:13]3[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]([NH:21][C@H:22]([C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]5)=[CH:26][CH:25]=4)[CH3:23])[N:14]=3)=[CH:11][N:12]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[Na].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[OH:3][CH:1]([C:4]1[C:5]2[N:6]([C:10]([C:13]3[C:18]([C:19]#[N:20])=[CH:17][N:16]=[C:15]([NH:21][C@H:22]([C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]5)=[CH:26][CH:25]=4)[CH3:23])[N:14]=3)=[CH:11][N:12]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 68688554HCID 68688554, compound

Product 1

HCID 11554545HCID 11554545, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

39 mg of the 4-(8-acetylimidazo[1,2-a]pyridin-3-yl)-2-{[(1S)-1-(4-piperazin-1-ylphenyl)ethyl]amino}pyrimidine-5-carbonitrile [156-3] was dissolved in a mixture solvent of 1 mL of tetrahydrofuran and 1 mL of methanol, then 2.8 mg of sodium boronhydride was added thereto, and stirred at room temperature for 15 minutes. Thereto, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insolubles were filtered, and then the filtrate was concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer chromatography, and 31.9 mg of 4-[8-(1-hydroxyethyl)imidazo[1,2-a]pyridin-3-yl]-2-{[(1S)-1-(4-piperazin-1-ylphenyl)ethyl]amino}pyrimidine-5-carbonitrile [156-4] was obtained as a two kinds of diastereomer mixture.

Workup

  1. extractionthe mixture was extracted with a mixture solvent of chloroform and methanol (chloroform:methanol=9:1)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insolubles were filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-b1a8e8f079794739a6f7b4637a70b421
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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