Ethanol → HCID 59398056, compound

HRID 2193228Notes

Reaction equation

HRID 2193228 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 702EthanolHCID 14797Potassium Hydroxide2×HCID 312751,4-DioxaneHCID 67539017HCID 67539017, compound

Product 1

HCID 59398056HCID 59398056, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.5 mL of a 1,4-dioxane solution containing 90 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, 2 mL of the solution was added and for 9.5 hours, 1 mL of the solution was added and for 1 hour, 1 mL of the solution was added and for 8 hours, further 1 mL of the solution was added and refluxed with heating for 3 hours. The reaction mixture was cooled to the room temperature, and the solvent was removed under reduced pressure. The residue was adjusted to pH 11 with 2.0 mol/L hydrochloric acid and ethyl acetate was added. The organic layer was separated, and 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 53 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 3 hours
  8. customthe solvent was removed under reduced pressure
  9. additionwas added
  10. customThe organic layer was separated
  11. washwashed with aqueous saturated sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customthe solvent was removed under reduced pressure
  14. customTo the residue thus obtained
  15. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-9980737ce4164a9bba7fa87b884d4c46
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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