Dimethylformamide → HCID 57562597, compound

HRID 1725476Notes

Reaction equation

HRID 1725476 reaction equation
[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[N:15][CH:14]=2)=[N:8]1.CN(C)C=O.[BH4-].[Na+]>O>[CH3:1][Si:2]([CH3:23])([CH3:22])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2[N:18]=[C:17]([CH2:19][OH:20])[CH:16]=[N:15][CH:14]=2)=[N:8]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 57562612HCID 57562612, compound

Product 1

HCID 57562597HCID 57562597, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 28 mg of 6-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)amino)pyrazine-2-carboxylic acid and 1 ml of N,N-dimethylformamide was added 84 mg of N,N′-carbonyldiimidazole, followed by stirring at room temperature for 15 hours. Then, 200 μl of an aqueous solution of 20 mg of sodium borohydride was added thereto and the resulting mixture was stirred. Water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1) to give the title compound.

Workup

  1. stirringthe resulting mixture was stirred
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe resulting ethyl acetate solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-cc0b55543faa41a092565b603834f48f
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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