Pyridine → HCID 2108389, compound

HRID 130485Notes

Reaction equation

HRID 130485 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.N1C=CC=CC=1.[C:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)(=[O:21])[CH3:20]>C1COCC1>[C:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)(=[O:30])=[O:29])=[CH:26][CH:27]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 2664184-Acetylbenzenesulfonyl chlorideHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 2108389HCID 2108389, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Trifluoromethoxy aniline (3.4 g, 19.21 mmol)was dissolved in THF (25 ml) before pyridine (4.44 ml, 54.88 mmol) was added. 4-Acetyl-benzenesulfonyl chloride (4.0 g, 18.29 mmol) was then added as a solid, and the resulting dark solution was stirred for 10 minutes. The volatiles were then removed, and the resulting residue was suspended in THF. Excess Et3N was then added, and the mixture was stirred for several minutes before the solids were filtered. The mother liquor was then evaporated to a solid which was purified by flash chromatography (EtOAc/hexanes) to yield the desired compound as a white solid. (5.5 g (15.31 mmol, 84%).

Workup

  1. additionwas added
  2. customThe volatiles were then removed
  3. additionExcess Et3N was then added
  4. stirringthe mixture was stirred for several minutes before the solids
  5. filtrationwere filtered
  6. customThe mother liquor was then evaporated to a solid which
  7. customwas purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-1655657cecd2442fafb5cdd6436b3a06
Source dataset
uspto-grants-2008_06
Patent number
US07381749B2

Reaction notes

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