Acetic Acid → HCID 66747631, compound

HRID 1748063Notes

Reaction equation

HRID 1748063 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:20]4=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]4[CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=[CH:4][CH2:3]1.CC(O)=O>C1COCC1.[Pt](=O)=O>[CH3:1][C:2]1([CH3:27])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[C:20]4=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]4[CH2:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66749333HCID 66749333, compound

Product 1

HCID 66747631HCID 66747631, compoundYield 10.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Platinum(IV) oxide (40 mg) was added to a solution of 9-{4-[(4,4-dimethylcyclohex-1-en-1-yl)oxy]phenyl}-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (340 mg) in THF (dry) (30 mL), NeOH (30 mL) and AcOH (10 mL). The mixture was stirred at room temperature under hydrogen overnight. Activated carbon was added and the insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc, to remove catalytic poison). Platinum(IV) oxide (40 mg) was added and the mixture was stirred at 50° C. under hydrogen for 6 hr. Platinum(IV) oxide was added and the mixture was stirred 50° C. under hydrogen for 12 hr. The insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc) and the filtrate was concentrated in vacuo with silica-gel. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from EtOAc/hexane. This was dissolved in THF, silica-gel was added to the solution and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with MeOH in EtOAc). The residue was crystallized from THF-EtOAc/IPE to give the title compound (37.6 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, to remove catalytic poison)
  3. additionPlatinum(IV) oxide (40 mg) was added
  4. stirringthe mixture was stirred at 50° C. under hydrogen for 6 hr
  5. additionPlatinum(IV) oxide was added
  6. stirringthe mixture was stirred 50° C. under hydrogen for 12 hr
  7. customThe insoluble solid was removed by filtration through silica gel/Celite pad (eluted with EtOAc)
  8. concentrationthe filtrate was concentrated in vacuo with silica-gel
  9. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  10. concentrationconcentrated in vacuo
  11. customThe residue was crystallized from EtOAc/hexane
  12. dissolutionThis was dissolved in THF
  13. additionsilica-gel was added to the solution
  14. customthe volatiles were removed in vacuo
  15. customwas purified by column chromatography (silica gel, eluted with MeOH in EtOAc)
  16. customThe residue was crystallized from THF-EtOAc/IPE

Sources & evidence

ORD record
ord-146e28ac4ecf470cb07cd63beee8f2ea
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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