Ethanol → HCID 59398056, compound

HRID 39854Notes

Reaction equation

HRID 39854 reaction equation
[O:1]1CCOCC1.[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][NH:18][CH:19]3[CH2:24][CH2:23][C:22]([CH2:27][CH2:28][N:29]4[C:38]5[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=5)[C:32]([CH3:41])=[CH:31][C:30]4=[O:42])([C:25]#[N:26])[CH2:21][CH2:20]3)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1.[OH-].[K+].C(O)C>C(OCC)C>[O:7]1[C:12]2[CH:13]=[CH:14][C:15]([CH2:17][NH:18][CH:19]3[CH2:24][CH2:23][C:22]([CH2:27][CH2:28][N:29]4[C:38]5[C:33](=[CH:34][CH:35]=[C:36]([O:39][CH3:40])[CH:37]=5)[C:32]([CH3:41])=[CH:31][C:30]4=[O:42])([C:25]([NH2:26])=[O:1])[CH2:21][CH2:20]3)=[CH:16][C:11]=2[O:10][CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14797Potassium Hydroxide6×HCID 312751,4-DioxaneHCID 67539017HCID 67539017, compound

Product 1

HCID 59398056HCID 59398056, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1 mL of a 1,4-dioxane solution containing 30 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarbonitrile, 1 mL of 20% aqueous potassium hydroxide solution and 1 mL of ethanol were added at room temperature and refluxed with heating for 4 hours. Further, 1 mL of 20% aqueous potassium hydroxide solution was added and refluxed with heating for 4 hours, thereafter 1.5 mL of 20% aqueous potassium hydroxide solution was further added and refluxed with heating for 9.5 hours. After 1 mL of 20% aqueous potassium hydroxide solution and 0.5 mL of ethanol were added and refluxed with heating for 1 hour, further 1 mL of 20% aqueous potassium hydroxide solution was added and refluxed with heating for 8 hours. After 1 mL of 20% aqueous potassium hydroxide solution was added and refluxed with heating for 6 hours, the reaction mixture was cooled to the room temperature, the solvent was removed under reduced pressure. The residue was adjusted to pH 11 with 2.0 mol/L hydrochloric acid and chloroform was added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, diethyl ether was added, and the resulting solid was filtered to give 21 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)cyclohexanecarboxamide as a white solid.

Workup

  1. additionwere added at room temperature
  2. temperaturerefluxed
  3. temperaturewith heating for 4 hours
  4. temperaturerefluxed
  5. temperaturewith heating for 4 hours
  6. temperaturerefluxed
  7. temperaturewith heating for 9.5 hours
  8. temperaturerefluxed
  9. temperaturewith heating for 1 hour
  10. temperaturerefluxed
  11. temperaturewith heating for 8 hours
  12. temperaturerefluxed
  13. temperaturewith heating for 6 hours
  14. customthe solvent was removed under reduced pressure
  15. additionwas added
  16. customThe organic layer was separated
  17. extractionthe aqueous layer was extracted with chloroform
  18. washwashed with aqueous saturated sodium chloride solution
  19. dry with materialdried over anhydrous magnesium sulfate
  20. customthe solvent was removed under reduced pressure
  21. customTo the residue thus obtained
  22. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-b3800d3d4a4d47b5aade6287fe2288ea
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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