HCID 66748610, compound → HCID 66748378, compound

HRID 1622735Notes

Reaction equation

HRID 1622735 reaction equation
[Br:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28]>C1COCC1.[Pt](=O)=O>[Br:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[C:18]4=[N:19][S:20](=[O:24])(=[O:23])[CH2:21][CH2:22][N:17]4[CH2:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28]

Participants

4

Reactant 1

HCID 66748610HCID 66748610, compound

Product 1

HCID 66748378HCID 66748378, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of platinum(IV) oxide (30 mg) and 9-{4-[4-bromo-3-(trifluoromethyl)phenoxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (192 mg) in THF (20 mL) was stirred under a hydrogen atmosphere overnight. To the reaction mixture was added activated carbon, and the mixture was filtered through basic silica gel and celite. To the filtrate was added silica gel and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) and concentrated under reduced pressure. The residue was separated by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA containing system)). To the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from THF and diisopropyl ether to give the title compound (30 mg) as a white solid.

Workup

  1. additionTo the reaction mixture was added
  2. filtrationthe mixture was filtered through basic silica gel and celite
  3. additionTo the filtrate was added silica gel
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated by HPLC (C18, mobile phase: water/acetonitrile (0.1% TFA containing system))
  8. additionTo the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe obtained residue was crystallized from THF and diisopropyl ether

Sources & evidence

ORD record
ord-555e0a59d21f48ea9a6355e6d08900f0
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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