Hydrochloric Acid → HCID 89690135, compound

HRID 517914Notes

Reaction equation

HRID 517914 reaction equation
[OH:1][C:2]1([CH3:37])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH2:4][CH2:3]1.[OH-].[Na+].Cl>CCO>[OH:1][C:2]1([CH3:37])[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=3)[N:10]=2)[N:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 89689894HCID 89689894, compound

Product 1

HCID 89690135HCID 89690135, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 7-(8-hydroxy-8-methyl-2,3-di-p-tolyl-7,8-dihydropyrido[3,2-b]pyrazin-5(6H)-yl)heptanoate (step 1) (10 mg, 0.020 mmol) in EtOH (1 ml) was added 2M NaOH (aq) (0.040 ml, 0.080 mmol). The reaction mixture was stirred at RT overnight under an atmosphere of nitrogen. A further portion of 2M NaOH (aq) (0.040 ml, 0.080 mmol) was added and stirring continued overnight. The resulting mixture was treated with 2M HCl (aq) to adjust the pH to pH5. The organic solvent was removed under reduced pressure and the mixture was diluted with water (10 ml) and extracted with ethyl acetate (2×10 ml). The combined extracts were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by chromatography on silica eluting with iso-hexane/EtOAc to afford the titled compound;

Workup

  1. stirringstirring continued overnight
  2. customThe organic solvent was removed under reduced pressure
  3. additionthe mixture was diluted with water (10 ml)
  4. extractionextracted with ethyl acetate (2×10 ml)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography on silica eluting with iso-hexane/EtOAc

Sources & evidence

ORD record
ord-ff3757bace6e479e89eda6b98e51d7ff
Source dataset
uspto-grants-2015_08
Patent number
US09115129B2

Reaction notes

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