Potassium Phosphate, Tribasic → Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1353099Notes

Reaction equation

HRID 1353099 reaction equation
[CH:1]1([NH:4][CH:5]=[C:6]([C:12]([C:14]2[C:15](Cl)=[N:16][C:17]([Cl:21])=[C:18]([F:20])[CH:19]=2)=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[Cl:21][C:17]1[N:16]=[C:15]2[C:14]([C:12](=[O:13])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]2[CH:1]2[CH2:3][CH2:2]2)=[CH:19][C:18]=1[F:20]

Participants

4

Reactant 2

HCID 62657Potassium Phosphate, TribasicHCID 178471870HCID 178471870, compound

Product 1

HCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.0 g of ethyl 3-cyclopropylamino-2-(2,6-dichloro-5-fluoropyridine-3-carbonyl)acrylate was dissolved in 35 ml of acetonitrile under heating to 75˜80° C. 8.56 g (2.0 eq.) of K3PO4 was added in portions to the reaction mixture, which was then stirred at the same temperature for 1.5 hours. The reaction mixture was filtered under a reduced pressure and washed with 77 ml of dichloromethane. The filtrate was concentrated under a reduced pressure. The resulting residue was dissolved in 77 ml of dichloromethane and then washed with water. The organic layer was concentrated under a reduced pressure to give 6.17 g of ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (Yield: 98.5%).

Workup

  1. temperatureunder heating to 75˜80° C
  2. filtrationThe reaction mixture was filtered under a reduced pressure
  3. washwashed with 77 ml of dichloromethane
  4. concentrationThe filtrate was concentrated under a reduced pressure
  5. dissolutionThe resulting residue was dissolved in 77 ml of dichloromethane
  6. washwashed with water
  7. concentrationThe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c068a306e51444a293ae7e76028c1825
Source dataset
uspto-grants-2007_05
Patent number
US07220861B2

Reaction notes

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