Methanesulfonyl chloride → HCID 59152218, compound

HRID 605592Notes

Reaction equation

HRID 605592 reaction equation
[C:1]([N:5]1[C:9]([NH:10][C:11]2[N:16]=[C:15]([CH2:17]O)[CH:14]=[N:13][CH:12]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.CS([Cl:32])(=O)=O.[Cl-].[Li+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C)C=O>[C:1]([N:5]1[C:9]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][Cl:32])[N:16]=2)=[CH:8][CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 59152207{6-[(1-tert-Butyl-1H-pyrazol-5-yl)amino]pyrazin-2-yl}methanol

Product 1

HCID 59152218HCID 59152218, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 507.3 mg of (6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyrazin-2-yl)methanol in 6.8 ml of chloroform were successively added 1.08 ml of diisopropylethylamine and 0.24 ml of methylsulfonyl chloride under cooling with ice, followed by stirring the reaction mixture at room temperature for 1.5 hours. To the reaction mixture were successively added 442.9 mg of lithium chloride and 6.8 ml of N,N-dimethylformamide, followed by stirring the reaction mixture at room temperature for 2 hours. After diluting the reaction mixture with ethyl acetate, the ethyl acetate solution was successively washed with water and brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1-1/4) to give the title compound as a yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring the reaction mixture at room temperature for 2 hours
  3. washthe ethyl acetate solution was successively washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1-1/4)

Sources & evidence

ORD record
ord-da4cc4201fb94fba85a51db0a598893b
Source dataset
uspto-grants-2011_03
Patent number
US07915263B2

Reaction notes

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