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

HRID 1353108Notes

Reaction equation

HRID 1353108 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.[H-].[Na+].O>O1CCCC1>[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

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 178471870HCID 178471870, compound

Product 1

HCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 3.0 g of ethyl 3-cyclopropylamino-2-(2,6-dichloro-5-fluoropyridine-3-carbonyl)acrylate in 36.4 ml of anhydrous tetrahydrofuran was cooled to 10° C. 0.36 g (1.05 eq.) of 60% sodium hydride was added to the reaction mixture, which was then stirred for 18 hours at room temperature. The reaction mixture was cooled to 5˜10° C. 36.4 ml of water was added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was filtered under a reduced pressure and washed with water. The resulting wet cake was dried under a reduced pressure at 50° C. for 5 hours to give 2.34 g of ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (Yield: 87.3%).

Workup

  1. temperatureThe reaction mixture was cooled to 5˜10° C
  2. stirringwas then stirred for 30 minutes
  3. filtrationThe organic layer was filtered under a reduced pressure
  4. washwashed with water
  5. customThe resulting wet cake was dried under a reduced pressure at 50° C. for 5 hours

Sources & evidence

ORD record
ord-c4d15adb6e9e4997adc007b1b2a14875
Source dataset
uspto-grants-2007_05
Patent number
US07220861B2

Reaction notes

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