HCID 47174299, compound → HCID 178448624, compound

HRID 2042718Notes

Reaction equation

HRID 2042718 reaction equation
[CH2:1]([NH:5][C:6]1[CH:11]=[N:10][N:9]([CH3:12])[C:8](=[O:13])[C:7]=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[CH:11]=[N:10][N:9]([CH3:12])[C:8](=[O:13])[C:7]=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 47174299HCID 47174299, compoundHCID 54578953HCID 54578953, compound

Product 1

HCID 178448624HCID 178448624, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(butylamino)-4-chloro-2-methylpyridazin-3(2H)-one from Example 4A (250 mg, 1.16 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl isothiocyanate (375 mg, 1.51 mmol) in dioxane (20 mL) was heated at 70° C. for 12 hours and at 100° C. for 6 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 (CH2Cl2-Et2O 19:1)) to afford 110 mg of the title compound. MS (ESI) m/z 429 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography (CH2Cl2-Et2O 19:1))

Sources & evidence

ORD record
ord-eb446848884d40ffa48b0f2f1a164784
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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