Hydrochloric Acid → (E)-7-(2,3-Diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoic acid

HRID 406210Notes

Reaction equation

HRID 406210 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22][C:23]([O:25]C)=[O:24])[C:10]3=[N:9][C:8]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[Li+].[OH-].Cl>C1COCC1.O>[C:1]1([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[CH2:22][C:23]([OH:25])=[O:24])[C:10]3=[N:9][C:8]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 66665849(E)-Methyl 7-(2,3-diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoate

Product 1

HCID 66665765(E)-7-(2,3-Diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-methyl 7-(2,3-diphenyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)hept-3-enoate (step 2) (30 mg, 0.070 mmol) in THF (3 ml):MeOH (1 ml) was added LiOH (10.08 mg, 0.421 mmol) in water (1 ml). The reaction mixture was heated at reflux for 1.5 h. After cooling to RT, 2M HCl was added until the pH of the mixture was below pH 5. The volatile solvent was removed in vacuo and the resulting mixture was extracted with EtOAc (2×15 ml). The combined organic extracts were washed with water, dried over MgSO4 and concentrated in vacuo to afford the title compound;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 h
  3. customThe volatile solvent was removed in vacuo
  4. extractionthe resulting mixture was extracted with EtOAc (2×15 ml)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b84219509ab94d6aaac27b94ec568dbd
Source dataset
uspto-grants-2014_06
Patent number
US08754085B2

Reaction notes

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