Hydrochloric Acid → HCID 135621716, compound

HRID 1783315Notes

Reaction equation

HRID 1783315 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])[O-].[K+].[K+].[Cl:11]C(OCC)=O.C(OC([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[C:40]3[C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:33](=[O:41])[NH:32][C:31]=3[N:30]([CH3:42])[N:29]=2)[CH2:24][CH2:23]1)=O)C.C(OC(N1C2N(C)N=C(C3CCN(C(OCC)=O)CC3)C=2C2C=CC=CC=2C1=O)=O)C.Cl>C(O)(=O)C>[ClH:11].[NH:22]1[CH2:23][CH2:24][CH:25]([C:28]2[C:40]3[C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:33](=[O:41])[NH:32][C:31]=3[N:30]([CH3:42])[N:29]=2)[CH2:26][CH2:27]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 6451240Aluminum(III) ChlorideHCID 23084818HCID 23084818, compoundHCID 135621733HCID 135621733, compound

Product 1

HCID 135621716HCID 135621716, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After the completion of the dropwise addition, the mixture was stirred at room temperature for 4 hrs and ice-cooled. Aluminum chloride (13.6 g) was added to the reaction mixture, and the mixture was stirred overnight at room temperature. After the completion of the reaction, the reaction mixture was poured into ice-water, and potassium carbonate was added to alkalify the reaction mixture. An excess amount of ethyl chloroformate was added to the reaction mixture, and the mixture was stirred at room temperature. The insoluble material was remove by filtration, and the aqueous layer was extracted with chloroform. The organic layer was dried over magnesium sulfate, and the solvent was evaporated to give a mixture of 1-(1-ethoxycarbonylpiperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5(4H)-one and 4-ethoxycarbonyl-1-(1-ethoxycarbonylpiperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5-one as solid. Further purification was not performed and the mixture was used in the next reaction. The total amount of the above-mentioned mixture was dissolved in acetic acid (100 mL) and concentrated hydrochloric acid (100 mL), and the mixture was heated under reflux for 24 hrs. After the completion of the reaction, the solvent was evaporated, and the precipitated crystals were collected by filtration to give 1-(piperidin-4-yl)-3-methyl-pyrazolo[3,4-c]isoquinolin-5(4H)-one hydrochloride (3.7 g).

Workup

  1. additionAfter the completion of the dropwise addition
  2. temperatureice-cooled
  3. stirringthe mixture was stirred overnight at room temperature
  4. customAfter the completion of the reaction
  5. additionwas added
  6. stirringthe mixture was stirred at room temperature
  7. customThe insoluble material was remove by filtration
  8. extractionthe aqueous layer was extracted with chloroform
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customthe solvent was evaporated
  11. customto give
  12. customFurther purification
  13. customthe mixture was used in the next reaction
  14. temperatureunder reflux for 24 hrs
  15. customAfter the completion of the reaction
  16. customthe solvent was evaporated
  17. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9fca6ad6373e43cc9b3bee6b8366157a
Source dataset
uspto-grants-2009_03
Patent number
US07501412B2

Reaction notes

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