HCID 54578953, compound → HCID 178448626, compound

HRID 2042715Notes

Reaction equation

HRID 2042715 reaction equation
Br[C:2]1[C:7]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][N:5]=[CH:4][N:3]=1.[F:13][C:14]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:15]=1[C:16]([N:18]=[C:19]=[S:20])=[O:17]>O1CCOCC1>[CH2:9]([N:8]1[C:7]2[CH:6]=[N:5][CH:4]=[N:3][C:2]=2[S:20]/[C:19]/1=[N:18]\[C:16](=[O:17])[C:15]1[CH:21]=[C:22]([C:25]([F:28])([F:27])[F:26])[CH:23]=[CH:24][C:14]=1[F:13])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 54578953HCID 54578953, compoundHCID 86660229HCID 86660229, compound

Product 1

HCID 178448626HCID 178448626, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of product from Example 3A (270 mg, 1.17 mmol) and 2-fluoro-5-(trifluoromethyl)benzoyl isothiocyanate (322 mg, 1.29 mmol) in dioxane was heated at 60° C. for 12 hours. The mixture was then concentrated under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography (hexanes-EtOAc 1:2) to afford 380 mg of the title compound. MS (ESI) m/z 399 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous NaHCO3
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography (hexanes-EtOAc 1:2)

Sources & evidence

ORD record
ord-d2f25dc4458744f093b64cee5868de2b
Source dataset
uspto-grants-2013_11
Patent number
US08586596B2

Reaction notes

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