Lithium Hydroxide → 7-(2-Phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

HRID 406190Notes

Reaction equation

HRID 406190 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[C:1]1([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66665828Ethyl 7-(2-phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Product 1

HCID 566442717-(2-Phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of ethyl 7-(2-phenyl-3-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (1.07 g, 2.338 mmol) in THF (12 ml) and water (6 ml) was treated with LiOH (0.560 g, 23.38 mmol) and stirred at 70° C. for 18 hours. After cooling to RT, the reaction mixture was concentrated in vacuo. The residue was diluted with water (20 ml) and the pH was adjusted to pH˜4 using 2M HCl. The aqueous portion was extracted with EtOAc (2×20 ml). The organic extracts were washed with brine, dried (MgSO4) and evaporated under vacuum. The residue was dissolved in hot (˜80° C.) ethanol (20 ml) and water (˜15 ml) was added until the solution became turbid. Upon cooling a solid precipitated. The mixture was kept cold for 72 hours. The solid was collected by filtration, washed with water and dried at 40° C. for 5 hours to afford the title compound;

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with water (20 ml)
  4. extractionThe aqueous portion was extracted with EtOAc (2×20 ml)
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under vacuum
  8. dissolutionThe residue was dissolved in hot (˜80° C.) ethanol (20 ml) and water (˜15 ml)
  9. additionwas added until the solution
  10. temperatureUpon cooling a solid
  11. customprecipitated
  12. waitThe mixture was kept cold for 72 hours
  13. filtrationThe solid was collected by filtration
  14. washwashed with water
  15. customdried at 40° C. for 5 hours

Sources & evidence

ORD record
ord-688ce2ed721b4b95829704e5befec72d
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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