Pyrrolidine → HCID 67313348, compound

HRID 1010885Notes

Reaction equation

HRID 1010885 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]3[N:24]4[CH:25]=[CH:26][CH:27]=[C:28]([CH3:29])[C:23]4=[N:22][CH:21]=3)[C:17]([C:30]#[N:31])=[CH:16][N:15]=2)[CH3:12])=[CH:7][CH:6]=1)=[O:4].[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:29][C:28]1[C:23]2[N:24]([C:20]([C:18]3[C:17]([C:30]#[N:31])=[CH:16][N:15]=[C:14]([NH:13][C@H:11]([C:8]4[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:32]5[CH2:36][CH2:35][CH2:34][CH2:33]5)=[CH:6][CH:7]=4)[CH3:12])[N:19]=3)=[CH:21][N:22]=2)[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 86625211HCID 86625211, compound

Product 1

HCID 67313348HCID 67313348, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20 mg of the compound [3-2] was dissolved in 0.4 mL of N,N-dimethylformamide, and 7 μL of pyrrolidine was added thereto. The reaction mixture was stirred for 30 minutes at room temperature, and then thereto was added a saturated aqueous solution of sodium hydrogen carbonate, and the mixture was extracted with chloroform. The resulting organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The insolubles were filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin-layer chromatography, to obtain 3 mg of 4-(8-methylimidazo[1,2-a]pyridin-3-yl)-2-({(1S)-1-[4-(pyrrolidin-1-ylacetyl) phenyl]ethyl}amino)pyrimidine-5-carbonitrile [3-3] (hereinafter, referred to as the compound [3-3]) as a colorless oily product.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe resulting 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 resulting residue was purified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-60cd8e9b9b9e48e79df988c1fe8f40dd
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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