Water → HCID 18549167, compound

HRID 1266172Notes

Reaction equation

HRID 1266172 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:18]2[N:17]=[C:16]3[C:19]([F:25])=[C:20](F)[C:21]([F:23])=[CH:22][C:15]3=[CH:14][C:13]=2[C:12](=[O:26])[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10]1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1.O>CS(C)=O>[F:23][C:21]1[C:20]([N:42]2[CH2:41][CH2:40][N:39]([C:36]3[CH:35]=[CH:34][C:33]([F:32])=[CH:38][CH:37]=3)[CH2:44][CH2:43]2)=[C:19]([F:25])[C:16]2=[N:17][C:18]3[N:9]([C:3]4[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=4[F:1])[CH:10]=[C:11]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12](=[O:26])[C:13]=3[CH:14]=[C:15]2[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 752601-(4-Fluorophenyl)piperazineHCID 18549168HCID 18549168, compound

Product 1

HCID 18549167HCID 18549167, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1.5 g of ethyl 1-(2,4-difluorophenyl)-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate and 1.8 g of 4-(4-fluorophenyl)piperazine in 20 cm3 of dimethyl sulphoxide was heated, with stirring, at a temperature around 100° C. for approximately 1 hour. After cooling to approximately 20° C., the reaction mixture was poured into 100 cm3 of water and extracted 3 times with 50 cm3 of trichloromethane. The combined organic extracts were washed 1 time with 50 cm3 of water, dried over magnesium sulphate and concentrated under reduced pressure (20 kPa) at a temperature around 40° C. 1.7 g of ethyl 7,9-difluoro-1-(2,4-difluorophenyl)-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at about 298-299° C., which solid was used without additional purification in the subsequent stages.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling to approximately 20° C.
  3. extractionextracted 3 times with 50 cm3 of trichloromethane
  4. washThe combined organic extracts were washed 1 time with 50 cm3 of water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure (20 kPa) at a temperature around 40° C

Sources & evidence

ORD record
ord-8213a1dfe5454709a6fed00c31840374
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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