Hydrochloric Acid → HCID 66795324, compound

HRID 1012274Notes

Reaction equation

HRID 1012274 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:33]=[CH:32][C:31]([C:34]([O:36]CC)=[O:35])=[N:30][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]([CH2:21][C:22](=[O:29])[N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[ClH:41]>O1CCCC1.CO>[ClH:41].[ClH:41].[CH:1]1([C:7]2[C:8]3[CH:33]=[CH:32][C:31]([C:34]([OH:36])=[O:35])=[N:30][C:9]=3[N:10]3[C:16]=2[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N:13]([CH2:21][C:22](=[O:29])[N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[CH2:12][CH2:11]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23152303HCID 23152303, compound

Product 1

HCID 66795324HCID 66795324, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 12-cyclohexyl-5-[2-oxo-2-(morpholin-4-yl)ethyl]-6,7-dihydro-5H-5,7a,8-triazadibenzo[a,e]azulene-9-carboxylate (62 mg, 0.12 mmol) in tetrahydrofuran (3 ml) and methanol (3 ml) was added 4N aqueous sodium hydroxide solution (1.5 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. 2N Hydrochloric acid (3 ml) was added to the reaction mixture to adjust to pH 7, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (chloroform:methanol=8:1) and the solvent was evaporated under reduced pressure. To a solution of the residue in ethyl acetate (1 ml) was added 4N HCl-ethyl acetate solution (1 ml) and the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the precipitated solid was collected by filtration, washed with hexane and dried in vacuo to give 12-cyclohexyl-5-[2-oxo-2-(morpholin-4-yl)ethyl]-6,7-dihydro-5H-5,7a,8-triazadibenzo[a,e]azulene-9-carboxylic acid dihydrochloride (20 mg, yield 30%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=8:1)
  8. customthe solvent was evaporated under reduced pressure
  9. additionTo a solution of the residue in ethyl acetate (1 ml) was added 4N HCl-ethyl acetate solution (1 ml)
  10. customthe solvent was evaporated under reduced pressure
  11. additionHexane was added to the residue
  12. filtrationthe precipitated solid was collected by filtration
  13. washwashed with hexane
  14. customdried in vacuo

Sources & evidence

ORD record
ord-902bd03a349c43248f072f6c4b8a0efc
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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