Cyclohexanecarbonyl chloride → Fuzapladib

HRID 2226451Notes

Reaction equation

HRID 2226451 reaction equation
[NH2:1][C:2]1[C:3]([NH:12][S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH:18]1([C:24](Cl)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH2:16]([S:13]([NH:12][C:3]1[C:2]([NH:1][C:24]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:25])=[CH:7][C:6]([C:8]([F:11])([F:9])[F:10])=[CH:5][N:4]=1)(=[O:15])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 10730665N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide

Product 1

HCID 154529FuzapladibYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.36 g of N-(3-amino-5-trifluoromethyl-2-pyridyl)ethanesulfonamide was dissolved in 24 ml of dry tetrahydrofuran, and 1.54 g of cyclohexanecarbonyl chloride was dropwise added thereto under cooing with ice. After the dropwise addition, the mixture was stirred for one hour and further reacted at room temperature overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, the obtained crystals were washed with ethyl ether to obtain 2.94 g of the desired product having a melting point of from 153° to 155° C.

Workup

  1. additionAfter the dropwise addition
  2. customfurther reacted at room temperature overnight
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. washthe obtained crystals were washed with ethyl ether

Sources & evidence

ORD record
ord-857a7914126b45dea199ae7f18d91bbd
Source dataset
uspto-grants-1994_09
Patent number
US05348967

Reaction notes

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