Acetyl chloride → N-({6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}sulphonyl)acetamide

HRID 2359921Notes

Reaction equation

HRID 2359921 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1.[H-].[Na+].[C:24](Cl)(=[O:26])[CH3:25]>C(#N)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH:11]=[C:10]([C:12]3[N:17]=[C:16]([S:18]([NH:21][C:24](=[O:26])[CH3:25])(=[O:19])=[O:20])[CH:15]=[CH:14][CH:13]=3)[CH:9]=[N:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 666336316-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridine-2-sulphonamide

Product 1

HCID 66633754N-({6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}sulphonyl)acetamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-[1-(Pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-sulphonamide (0.15 g, 0.44 mmol) was initially charged in acetonitrile (1.5 ml) under argon, and sodium hydride (0.026 g, 0.66 mmol, 60%) was added in portions. The reaction mixture was stirred at room temperature for 1 h, then acetyl chloride (0.052 g, 0.66 mmol) was added dropwise. The reaction mixture was stirred at 82° C. for 33 h and, after cooling, the solvent was removed under reduced pressure. The residue was taken up in saturated sodium hydrogencarbonate solution, dichloromethane was added and the precipitated solid was filtered off. The phases of the filtrate were separated; the aqueous phase was adjusted to pH 3 with hydrochloric acid and left to stand for 16 h. The precipitated crystals were filtered off with suction. Yield 0.02 g (12% of theory) of N-({6-[1-(pyridin-3-yl)-1H-pyrazol-4-yl]pyridin-2-yl}sulphonyl)acetamide.

Workup

  1. stirringThe reaction mixture was stirred at 82° C. for 33 h
  2. temperatureafter cooling
  3. customthe solvent was removed under reduced pressure
  4. additiondichloromethane was added
  5. filtrationthe precipitated solid was filtered off
  6. customThe phases of the filtrate were separated
  7. waitleft
  8. waitto stand for 16 h
  9. filtrationThe precipitated crystals were filtered off with suction

Sources & evidence

ORD record
ord-5b3e2c1824de4524a03dc5d630797b04
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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