HCID 66748070, compound → HCID 66748136, compound

HRID 2035885Notes

Reaction equation

HRID 2035885 reaction equation
[F:1][C:2]([F:28])([C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3=[N:15][S:16](=[O:20])(=[O:19])[CH2:17][CH2:18][N:13]3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1>C1COCC1.CO.[Pt](=O)=O>[F:28][C:2]([F:1])([C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]3=[N:15][S:16](=[O:20])(=[O:19])[CH2:17][CH2:18][N:13]3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 66748070HCID 66748070, compound

Product 1

HCID 66748136HCID 66748136, compoundYield 45.7%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (30 mg) was added to a solution of 9-{4-[difluoro(4-methylphenyl)methyl]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (156 mg) in THF (dry) (20 mL) and MeOH (20 mL). The mixture was stirred at room temperature under hydrogen for 3 h. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). Platinum(IV) oxide (30 mg) was added and the mixture was stirred at room temperature under hydrogen overnight. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (72.0 mg) as colorless crystals.

Workup

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  3. additionPlatinum(IV) oxide (30 mg) was added
  4. stirringthe mixture was stirred at room temperature under hydrogen overnight
  5. additionActivated carbon was added
  6. customthe insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc)
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was crystallized from THF/IPE

Sources & evidence

ORD record
ord-744322e93a524c3f9845eaddae1f5b39
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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