Pyridine → HCID 14700567, compound

HRID 1084365Notes

Reaction equation

HRID 1084365 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]([CH2:19][CH3:20])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.N1C=CC=CC=1.[CH3:29][CH:30]1[CH2:35][NH:34][CH2:33][CH2:32][NH:31]1>C(O)C>[CH2:19]([N:9]1[C:8]2[N:7]=[C:6]3[CH:21]=[C:2]([N:34]4[CH2:33][CH2:32][NH:31][CH:30]([CH3:29])[CH2:35]4)[C:3]([F:22])=[CH:4][C:5]3=[CH:14][C:13]=2[C:12](=[O:15])[C:11]([C:16]([OH:18])=[O:17])=[CH:10]1)[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 660572-MethylpiperazineHCID 147005558-Chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 14700567HCID 14700567, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Ethyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid is prepared under the conditions of Example 1 but starting from 2.1 g of 8-chloro-1-ethyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylic acid, 20 cm3 of pyridine and 2.4 g of 2-methylpiperazine. After taking up in ethanol and concentrating to dryness under reduced pressure (20 kPa at 50° C.), the solid residue is taken up in 20 cm3 of water and 10 cm3 of 2 N potassium hydroxide solution. The aqueous solution obtained is washed with twice 20 cm3 of trichloromethane, 10 cm3 of acetic acid are added and the mixture is again washed with twice 40 cm3 of trichloromethane. 23 cm3 of 4.5 N potassium hydroxide solution are added and the suspension obtained is heated to a temperature close to 90° C. After cooling to a temperature close to 20° C., the precipitate is drained and washed with 3 times 10 cm3 of water and twice 10 cm3 of ethanol. After recrystallizing twice from 120 cm3 of dimethylformamide each time, 1.7 g of 1-ethyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid are obtained in the form of a yellow solid melting at 310°-312° C.

Workup

  1. concentrationconcentrating to dryness under reduced pressure (20 kPa at 50° C.)
  2. customThe aqueous solution obtained
  3. washis washed with twice 20 cm3 of trichloromethane, 10 cm3 of acetic acid
  4. additionare added
  5. washthe mixture is again washed with twice 40 cm3 of trichloromethane
  6. addition23 cm3 of 4.5 N potassium hydroxide solution are added
  7. customthe suspension obtained
  8. temperatureis heated to a temperature
  9. customclose to 90° C
  10. temperatureAfter cooling to a temperature
  11. customclose to 20° C.
  12. washwashed with 3 times 10 cm3 of water and twice 10 cm3 of ethanol
  13. customAfter recrystallizing twice from 120 cm3 of dimethylformamide each time, 1.7 g of 1-ethyl-7-fluoro-8-(3-methyl-1-piperazinyl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Sources & evidence

ORD record
ord-3b3c11a51ba243a193081887cd072df8
Source dataset
uspto-grants-1991_04
Patent number
US05004745

Reaction notes

Loading…