Pyridine → 1-[2-(2-Ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidin-4-yl]-2-tosylhydrazine

HRID 521675Notes

Reaction equation

HRID 521675 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:22]=[C:23]([NH:35][NH2:36])[C:24]2[N:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:25]=2[N:26]=1)[CH3:13].N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(#N)C>[CH2:12]([S:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[N:22]=[C:23]([NH:35][NH:36][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C:24]2[N:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:25]=2[N:26]=1)[CH3:13]

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 118035279HCID 118035279, compound

Product 1

HCID 1180349901-[2-(2-Ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidin-4-yl]-2-tosylhydrazineYield 44.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

152 mg of p-toluenesulfonyl chloride was added to a mixture of 246 mg of [2-(2-ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidin-4-yl]-hydrazine, 74 mg of pyridine and 5 ml of acetonitrile, under ice cooling, and the mixture was stirred at room temperature for 15 minutes. A saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was washed with t-butyl methyl ether and n-hexane, and then dried to obtain 156 mg of 1-[2-(2-ethylsulfanylphenyl)-7-trifluoromethylpyrido[3,2-d]pyrimidin-4-yl]-2-tosylhydrazine.

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting residue was washed with t-butyl methyl ether and n-hexane
  6. customdried

Sources & evidence

ORD record
ord-60d57912394b48d899decccbf4a0b70a
Source dataset
uspto-grants-2016_05
Patent number
US09328121B1

Reaction notes

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