A-425619 → HCID 69522424, compound

HRID 1181445Notes

Reaction equation

HRID 1181445 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([NH:11][C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[O:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH:26]OS([O-])=O.[K+]>C(Cl)(Cl)Cl>[O-:26][N+:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)=[O:13])[CH:1]=1

Participants

4

Reactant 2

HCID 8068410A-425619HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 69522424HCID 69522424, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of N-isoquinolin-5-yl-N′-[4-(trifluoromethyl)benzyl]urea (Example 14; 100 mg, 0.29 mmol) in chloroform (25 ml) was added Oxone (541 mg, 0.87 mmol), followed by wet alumina Grade III (1 g), and the resulting suspension heated at reflux for 60 minutes. Whilst the mixture was still hot it was filtered to remove alumina and Oxone, the solids were washed with more chloroform, then methanol, and the filtrate evaporated to dryness. The residue was purified by preparative TLC eluting with 10% MeOH in dichloromethane+0.5% NH4OH, and the product triturated with a mixture of dichloromethane/iso-hexanes, filtered and dried to give the title compound (11 mg, 10%) as a white solid. m/z (ES+) 362 (M+H)+.

Workup

  1. temperaturethe resulting suspension heated
  2. temperatureat reflux for 60 minutes
  3. filtrationwas filtered
  4. customto remove alumina and Oxone
  5. washthe solids were washed with more chloroform
  6. custommethanol, and the filtrate evaporated to dryness
  7. customThe residue was purified by preparative TLC
  8. washeluting with 10% MeOH in dichloromethane+0.5% NH4OH
  9. customthe product triturated with a mixture of dichloromethane/iso-hexanes
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-0e579f81713b4e919e4802fba7158156
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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