Hydrochloric Acid → HCID 178490517, compound

HRID 2225599Notes

Reaction equation

HRID 2225599 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[N:4]1.[CH3:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:31])[CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27]Cl)=[C:21]([O:29][CH3:30])[CH:20]=2)[CH2:11][CH2:10]1.Cl>C1COCC1.C(Cl)Cl>[CH3:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH:15][C:16](=[O:31])[CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][C:7]3[CH:6]=[CH:5][NH:4][N:3]=3)=[C:21]([O:29][CH3:30])[CH:20]=2)[CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1048PyrazoleHCID 24758Sodium hydrideHCID 178490530HCID 178490530, compound

Product 1

HCID 178490517HCID 178490517, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 g of sodium hydride was added to a solution of 0.68 g of pyrazole in 50 ml of THF. Next, 1.9 g of N-(trans-4-methylcyclohexyl)-4-(2-chloroethoxy)-3-methoxycinnamamide (Example 138) was added to the solution. The solution was reacted for 24 hours, while it was refluxed. After reaction, 2 N hydrochloric acid was added, acidifying the reaction solution. The solution was washed with 100 ml of methylene chloride. Ammonia water was added to the aqueous layer obtained, alkalizing the solution. Thereafter, the solution was extracted with 100 ml of methylene chloride. The organic layer obtained was dried over magnesium sulfate, and the solvent was removed in vacuo. The product obtained was refined by means of silica gel column chromatography using methylene chloride only. Thereafter, the solvent was removed in vacuo, yielding 0.44 g of N-(trans-4-methylcyclohexyl)-4-(2-pyrazolylethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 24 hours, while it
  2. temperaturewas refluxed
  3. additionwas added
  4. washThe solution was washed with 100 ml of methylene chloride
  5. additionAmmonia water was added to the aqueous layer
  6. customobtained
  7. extractionThereafter, the solution was extracted with 100 ml of methylene chloride
  8. customThe organic layer obtained
  9. dry with materialwas dried over magnesium sulfate
  10. customthe solvent was removed in vacuo
  11. customThe product obtained
  12. customThereafter, the solvent was removed in vacuo

Sources & evidence

ORD record
ord-6bb02b05b6444a4cb59652542156e9eb
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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