HCID 66748429, compound → HCID 66747911, compound

HRID 1405801Notes

Reaction equation

HRID 1405801 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[C:22]5=[N:23][S:24](=[O:28])(=[O:27])[CH2:25][CH2:26][N:21]5[CH:20]=[CH:19][CH:18]=4)=[CH:13][CH:12]=3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1>C1COCC1.CO.[Pt](=O)=O>[O:1]1[C:5]2[CH:6]=[C:7]([O:10][C:11]3[CH:16]=[CH:15][C:14]([CH:17]4[C:22]5=[N:23][S:24](=[O:27])(=[O:28])[CH2:25][CH2:26][N:21]5[CH2:20][CH2:19][CH2:18]4)=[CH:13][CH:12]=3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 66748429HCID 66748429, compound

Product 1

HCID 66747911HCID 66747911, compoundYield 68.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (20 mg) was added to a solution of 9-[4-(2,3-dihydro-1-benzofuran-6-yloxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (100 mg) in THF (dry) (50 mL) and MeOH (50 mL). The mixture was stirred at room temperature under hydrogen for 3 hr. Activated carbon was added and the insoluble solid was removed by filtration through NH-silica gel/Celite pad (eluted with EtOAc). Platinum(IV) oxide (20 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 (68.8 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 (20 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-05507a7317d244e1878562a9c85de6a0
Source dataset
uspto-grants-2014_12
Patent number
US08916551B2

Reaction notes

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