Ethanol → HCID 70030230, compound

HRID 1266174Notes

Reaction equation

HRID 1266174 reaction equation
Cl[C:2]1[C:3]([F:22])=[CH:4][C:5]2[C:6]([CH:21]=1)=[N:7][C:8]1[N:9]([NH:19][CH3:20])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1.C(O)C>N1C=CC=CC=1>[F:22][C:3]1[C:2]([N:33]2[CH2:32][CH2:31][N:30]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[CH:29][CH:28]=3)[CH2:35][CH2:34]2)=[CH:21][C:6]2=[N:7][C:8]3[N:9]([NH:19][CH3:20])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=3[CH:14]=[C:5]2[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 752601-(4-Fluorophenyl)piperazineHCID 147005588-Chloro-7-fluoro-1-methylamino-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 70030230HCID 70030230, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7-Fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methylamino-4-oxo-1,4-dihydrobenzo[b][1,8]naph-thyridine-3-carboxylic acid was prepared under the conditions of Example 2, but from 3.2 g of 8-chloro-7-fluoro-1-methylamino-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 9 g of 4-(4-fluorophenyl)piperazine in 30 cm3 of pyridine for 28 hours. After concentrating the reaction mixture to dryness under reduced pressure (20 kPa) at approximately 60° C., the residue was taken up twice in 30 cm3 of ethanol and concentrated under reduced pressure under the above conditions. The solid was taken up into 50 cm3 of water and 10 cm3 of 30% aqueous potassium hydroxide solution. 20 cm3 of water and approximately 10 cm3 of 10% acetic acid were added to the precipitate formed. The suspension was extracted 3 times with 50 cm3 of trichloromethane. The trichloromethane was concentrated under reduced pressure (20 kPa) and the solid obtained was taken up in 2 times 20 cm3 of ethanol. After crystallizing once from 42 cm3 and then recrystallizing once from 15 cm3 of dimethylformamide, 1.33 g of 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methylamino-4-oxo-1,4-dihydrobenzo[b][1,8]naph-thyridine-3-carboxylic acid were obtained in the form of a brown solid melting at about 304-305° C.

Workup

  1. custom7-Fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methylamino-4-oxo-1,4-dihydrobenzo[b][1,8]naph-thyridine-3-carboxylic acid was prepared under the conditions of Example 2
  2. concentrationAfter concentrating the reaction mixture to dryness under reduced pressure (20 kPa) at approximately 60° C.
  3. concentrationconcentrated under reduced pressure under the above conditions
  4. addition20 cm3 of water and approximately 10 cm3 of 10% acetic acid were added to the precipitate
  5. customformed
  6. extractionThe suspension was extracted 3 times with 50 cm3 of trichloromethane
  7. concentrationThe trichloromethane was concentrated under reduced pressure (20 kPa)
  8. customthe solid obtained
  9. customAfter crystallizing once from 42 cm3
  10. customrecrystallizing once from 15 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-775c27c246a740cbb9bec17b5bb68378
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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