HCID 66747700, compound → 9-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

HRID 2035916Notes

Reaction equation

HRID 2035916 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][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]=[C:15]([CH3:25])[CH:14]=3)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:28][CH3:29]>C1COCC1.CO.[Pt](=O)=O>[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:8]=[CH:9][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][CH:15]([CH3:25])[CH2:14]3)=[CH:11][CH:12]=2)=[CH:4][C:3]=1[O:28][CH3:29]

Participants

5

Reactant 1

HCID 66747700HCID 66747700, compound

Product 1

HCID 667480489-[4-(4-Fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideYield 7.5%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (30 mg) was added to a solution of 9-[4-(4-fluoro-3-methoxyphenoxy)phenyl]-7-methyl-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (400 mg) in THF (dry) (15 ml) and MeOH (15 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 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. AcOH (10 mL) and platinum(IV) oxide (30 mg) were added and the mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (30.3 mg) as colorless crystals.

Workup

  1. additionActivated carbon was added
  2. customthe insoluble solid was removed by filtration through 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. additionAcOH (10 mL) and platinum(IV) oxide (30 mg) were added
  6. stirringthe mixture was stirred at room temperature under hydrogen for 1 day and at 50° C. for 1 day
  7. additionActivated carbon was added
  8. customthe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  9. concentrationthe filtrate was concentrated in vacuo
  10. customThe residue was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
  11. concentrationconcentrated in vacuo
  12. customThe residue was crystallized from THF/IPE

Sources & evidence

ORD record
ord-7d6809349be54967982da287a33eb1fb
Source dataset
uspto-grants-2013_11
Patent number
US08575154B2

Reaction notes

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