Propan-2-one--water (1/1) → [5-(4-Methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

HRID 908162Notes

Reaction equation

HRID 908162 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH3:7][C:8]1[N:9]=[C:10]([NH:21][C:22]2[CH:27]=[N:26][CH:25]=[CH:24][N:23]=2)[S:11][C:12]=1[C:13]1[CH:18]=[CH:17][C:16](SC)=[CH:15][CH:14]=1.[CH3:28]C(C)=O.O>>[CH3:28][S:3]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[S:11][C:10]([NH:21][C:22]3[CH:27]=[N:26][CH:25]=[CH:24][N:23]=3)=[N:9][C:8]=2[CH3:7])=[CH:14][CH:15]=1)(=[O:5])=[O:2]

Participants

4

Reactant 3

HCID 18366337Propan-2-one--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 86761401[4-Methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine

Product 1

HCID 85996781[5-(4-Methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-pyrazin-2-yl-amine

Procedure

Oxone (Potassium peroxymonosulfate) (0.417 g, 0.77 mmol) is added to a stirred solution of [4-methyl-5-(4-methylsulfanyl-phenyl)-thiazol-2-yl]-pyrazin-2-yl-amine (27c) (0.05 g, 0.16 mmol) in acetone-water (9:1). After 2 hours at room temperature the solid precipitate is removed by filtration. The solid is dissolved in methanol, filtered to remove oxone and the solvent is removed from the filtrate to afford the title compound as a yellow solid (0.022 g).

Workup

  1. customAfter 2 hours at room temperature the solid precipitate is removed by filtration
  2. dissolutionThe solid is dissolved in methanol
  3. filtrationfiltered
  4. customto remove oxone
  5. customthe solvent is removed from the filtrate

Sources & evidence

ORD record
ord-97040938820b4dd5903a482548d0b0b5
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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