Hydrochloric Acid → 1-(2,2-diethoxyethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one

HRID 1804733Notes

Reaction equation

HRID 1804733 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[N:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[CH2:22][CH:23]([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26].COC1CCCC1.Cl>CS(C)=O.O>[CH2:25]([O:24][CH:23]([O:27][CH2:28][CH3:29])[CH2:22][N:9]1[C:10]2[C:5](=[N:4][CH:3]=[C:2]([F:1])[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:12])[CH3:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 138539Cyclopentyl methyl etherHCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-one

Product 1

HCID 595107411-(2,2-diethoxyethyl)-7-fluoro-1,5-naphthyridin-2(1H)-oneYield 60.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of 3.00 g of 7-fluoro-1,5-naphthyridin-2(1H)-one and 5.04 g of potassium phosphate in 12 mL of dimethyl sulfoxide, 4.68 g of 2-bromo-1,1-diethoxyethane was added at room temperature, and the resultant mixture was stirred for 4.5 hours at 94° C. The reaction mixture was cooled, and 21 mL of water and 12 mL of cyclopentyl methyl ether were added thereto. The mixture was adjusted to pH 5.8 with 12 mol/L hydrochloric acid, subsequently the insoluble matter was filtered out, and the filter residue was washed twice with 3 mL of cyclopentyl methyl ether. The organic layers of the obtained filtrate and the wash liquid were separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 3.11 g of 1-(2,2-diethoxyethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one as a light yellow oily substance.

Workup

  1. additionwas added at room temperature
  2. temperatureThe reaction mixture was cooled
  3. filtrationsubsequently the insoluble matter was filtered out
  4. washthe filter residue was washed twice with 3 mL of cyclopentyl methyl ether
  5. customThe organic layers of the obtained filtrate and the wash liquid were separated
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4d79b727e42494ebd99dd80c8929ff0
Source dataset
uspto-grants-2013_01
Patent number
US08354426B2

Reaction notes

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