Methanol → 1-Cyclopentyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylic acid

HRID 253131Notes

Reaction equation

HRID 253131 reaction equation
[CH:1]1([N:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][C:8]([C:19]([O:21]C)=[O:20])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Li+].CO.OS(O)(=O)=O>O>[CH:1]1([N:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:9][C:8]([C:19]([OH:21])=[O:20])=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3939Lithium HydroxideHCID 66845912HCID 66845912, compound

Product 1

HCID 668448391-Cyclopentyl-6-oxo-5-(pyridin-2-yl)-1,6-dihydropyridine-3-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The pyridone (Step 3, 57 mg, 0.19 mmol) and lithium hydroxide (16 mg, 0.38 mmol) were stirred at room temperature in a solution of 2 mL of MeOH and 0.3 mL of H2O, for 2 h. The reaction mixture was diluted with water and the pH was adjusted to pH ˜2 with concentrated H2SO4. The mixture was extracted 3×20% IPA:CHCl3 and the combined organic fractions were dried over MgSO4 and concentrated. The crude residue was purified to obtain the title compound as a white powder (48 mg, 89%). MS m/z: 285 (M+1).

Workup

  1. extractionThe mixture was extracted 3×20% IPA
  2. dry with materialCHCl3 and the combined organic fractions were dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude residue was purified

Sources & evidence

ORD record
ord-0d7062303b2f4ddaaf704e9d9891c2b7
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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