Water → HCID 19365497, compound

HRID 849936Notes

Reaction equation

HRID 849936 reaction equation
[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([F:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)[CH:7]=1.O.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[Cl:21][C:3]1[C:2]([NH:1][S:24]([CH3:23])(=[O:26])=[O:25])=[CH:7][C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)=[C:5]([F:20])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 19365532HCID 19365532, compound2×

Product 1

HCID 19365497HCID 19365497, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Then, 0.10 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-23) was dissolved in 0.62 ml of pyridine, to which 36 μl of methanesulfonyl chloride was added dropwise, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was poured into water, followed by extraction with chloroform. The organic layer was washed with 2N hydrochloric acid, water, saturated sodium hydrogencarbonate solution, and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography, which afforded 91 mg (yield, 73%) of 3-[4-chloro-2-fluoro-5-(methanesulfonylamino)phenyl]-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-37; m.p., 168.5° C.).

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with 2N hydrochloric acid, water, saturated sodium hydrogencarbonate solution
  5. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fa49abd2f0b0437582eb149873a719fc
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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