Sodium hydride → HCID 86668789, compound

HRID 921295Notes

Reaction equation

HRID 921295 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9].[H-].[Na+].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][N:18]=1>CN(C)C=O>[Cl:16][C:17]1[N:18]=[C:19]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[C:20]([C:24]([F:27])([F:25])[F:26])=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27827742,4-Dichloro-5-(trifluoromethyl)pyrimidineHCID 126463662-(Propane-2-sulfonyl)aniline

Product 1

HCID 86668789HCID 86668789, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-Amino-2-(isopropylsulphonyl)benzene (350 mg, 1.6 mmol) in 4 mL of N,N-Dimethyl formamide at 0 degree, was added Sodium hydride (100 mg) and the reaction mixture was allowed to stirred at 0 degree for 20 minutes. 2,4-Dichloro-5-(trifluoromethyl)pyrimidine (350 mg, 1.6 mmol) was added in one portion and the reaction mixture was warmed to room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted with Ethyl acetate. The combined Ethyl acetate layers were dried over Sodium Sulfate and solvent was removed under reduced pressure. The residue was purified by Prep-HPLC to yield the desired product as a white solid (10 mg, 2% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with Ethyl acetate
  4. dry with materialThe combined Ethyl acetate layers were dried over Sodium Sulfate and solvent
  5. customwas removed under reduced pressure
  6. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-057260f1a0924c6eb25204fbfb322a40
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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