Sodium Hydroxide → HCID 117988056, compound

HRID 2206043Notes

Reaction equation

HRID 2206043 reaction equation
[CH:1]1([N:6]2[C:14]3[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][NH:11][C:10](=O)[C:9]=3[CH:8]=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>C(#N)C>[Cl:22][CH:10]1[C:9]2[CH:8]=[CH:7][N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:14]=2[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:12][NH:11]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 117987968HCID 117987968, compound

Product 1

HCID 117988056HCID 117988056, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate (1.83 g) obtained in Step D of Example 29 in acetonitrile (20 mL) was added phosphoryl chloride (4 mL), and the mixture was stirred at 80° C. for 4 hr. To the reaction mixture was added 8N aqueous sodium hydroxide solution at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.37 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-adfd15a628764d638664f5d4ce72231b
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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