Hydrochloric Acid → HCID 11518638, compound

HRID 2246689Notes

Reaction equation

HRID 2246689 reaction equation
[C:1]([C:3]1[C:7]([N:8]([CH3:16])[S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:6]([N:17]=CN(C)C)[N:5]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])[N:4]=1)#[N:2].Cl>CO>[NH2:17][C:6]1[N:5]([C:22]2[C:23]([Cl:33])=[CH:24][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:26][C:27]=2[Cl:28])[N:4]=[C:3]([C:1]#[N:2])[C:7]=1[N:8]([CH3:16])[S:9]([C:12]([F:13])([F:15])[F:14])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86623838HCID 86623838, compound

Product 1

HCID 11518638HCID 11518638, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-{[(dimethylamino)methylene]amino}-1H-pyrazol-4-yl)-1,1,1-trifluoro-N-methylmethanesulfonamide (240 mg, 0.45 mmol) in methanol (7 ml) was added hydrochloric acid (4N, 4 ml) and the reaction mixture was heated at reflux for 4 h. The reaction mixture was concentrated under nitrogen and the residue partitioned between ethyl acetate and water. The two layers were separated and the aqueous layer was extracted with ethyl acetate (×2). The combined organic phases were dried (MgSO4) and concentrated under nitrogen. The crude product was dissolved in acetonitrile (4 ml) and purified by automated preparative liquid chromatography (Gilson system, 150 mm×21.2 mm Phenomonex LUNA 100 Å C18 column) using an acetonitrile:water gradient [50:50 to 98:2]. The appropriate fractions were concentrated in vacuo to give the titled compound (105 mg).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction mixture was concentrated under nitrogen
  4. customthe residue partitioned between ethyl acetate and water
  5. customThe two layers were separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (×2)
  7. dry with materialThe combined organic phases were dried (MgSO4)
  8. concentrationconcentrated under nitrogen
  9. dissolutionThe crude product was dissolved in acetonitrile (4 ml)
  10. custompurified
  11. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-3004c011618146418fb9c0605dfacd1e
Source dataset
uspto-grants-2010_03
Patent number
US07687533B2

Reaction notes

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