HCID 54578953, compound → HCID 178448623, compound

HRID 2042717Notes

Reaction equation

HRID 2042717 reaction equation
[CH2:1]([NH:5][C:6]1[C:7](=[O:14])[N:8]([CH3:13])[N:9]=[CH:10][C:11]=1Cl)[CH2:2][CH2:3][CH3:4].[F:15][C:16]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:17]=1[C:18]([N:20]=[C:21]=[S:22])=[O:19]>O1CCOCC1>[CH2:1]([N:5]1[C:6]2[C:7](=[O:14])[N:8]([CH3:13])[N:9]=[CH:10][C:11]=2[S:22]/[C:21]/1=[N:20]\[C:18](=[O:19])[C:17]1[CH:23]=[C:24]([C:27]([F:30])([F:29])[F:28])[CH:25]=[CH:26][C:16]=1[F:15])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 54578953HCID 54578953, compoundHCID 67994474HCID 67994474, compound

Product 1

HCID 178448623HCID 178448623, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(butylamino)-5-chloro-2-methylpyridazin-3(2H)-one from Example 4A (130 mg, 0.60 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl isothiocyanate (248 mg, 1 mmol) in dioxane (20 mL) was heated at reflux for 72 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in EtOAc, washed with saturated aqueous NaHCO3 and brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (hexanes-EtOAc 3:1) to afford 100 mg of the title compound. MS (ESI) m/z 215 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 72 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with saturated aqueous NaHCO3 and brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography (hexanes-EtOAc 3:1)

Sources & evidence

ORD record
ord-ab4b1655037a43908d9d567bf9ce85dc
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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