Dimethylformamide dimethyl acetal → Ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 246954Notes

Reaction equation

HRID 246954 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22]([S:24][CH2:25][CH3:26])[C:21]([F:27])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13].[CH3:28]OC(OC)N(C)C>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2[C:11](=[CH:20][C:21]([F:27])=[C:22]([S:24][CH2:25][CH3:26])[N:23]=2)[C:12](=[O:13])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:28]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13849319Ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate

Product 1

HCID 13849337Ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateYield 70.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 3 ml of benzene was dissolved 160 mg of ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate, and 72 mg of N,N-dimethylformamide dimethylacetal was added thereto, after which the resulting mixture was subjected to reaction under reflux for 2.5 hours. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-ethyl acetate (10:1 by volume)] to obtain 115 mg (yield 70.1%) of ethyl 1-(2,4-difluorophenyl)-7-ethylthio-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate having a melting point of 169.5°-171° C.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2.5 hours
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-ethyl acetate (10:1 by volume)]

Sources & evidence

ORD record
ord-a5fd1edecadc451ca236fc60dbeccb00
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

Loading…