Pyridine → HCID 68543924, compound

HRID 1182175Notes

Reaction equation

HRID 1182175 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][CH:13]([CH3:15])[CH3:14])(=[O:11])=[O:10].N1C=CC=CC=1.[F:22][C:23]([F:35])([F:34])[O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([S:9]([NH:12][CH:13]([CH3:15])[CH3:14])(=[O:11])=[O:10])[C:2]=1[NH:1][C:29](=[O:30])[C:28]1[CH:32]=[CH:33][C:25]([O:24][C:23]([F:22])([F:34])[F:35])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 68546634HCID 68546634, compound

Product 1

HCID 68543924HCID 68543924, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.30 g (1.4 mmol) of the material from Step B in 5 mL of chloroform was added 0.28 ml (3.5 mmol) of pyridine and 0.27 mL (1.7 mmol) of 4-(trifluoromethoxy)benzoyl chloride. The reaction mixture was stirred overnight at room temperature and then heated at reflux for 5 hours. After cooling to room temperature the reaction mixture was washed with 1N HCl, dried (sodium sulfate) and filtered. The volatiles were removed with a rotary evaporator. The residue was purified by MPLC (5–25% ethyl acetate in hexanes as eluant) to afford 0.10 g of the title compound, a compound of the invention, as a white solid melting at 104–107° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. washwas washed with 1N HCl
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customThe volatiles were removed with a rotary evaporator
  8. customThe residue was purified by MPLC (5–25% ethyl acetate in hexanes as eluant)

Sources & evidence

ORD record
ord-b7844b86452b432e861e8095917f97c1
Source dataset
uspto-grants-2007_10
Patent number
US07288554B2

Reaction notes

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