Acetic Acid → RP60556A

HRID 1266156Notes

Reaction equation

HRID 1266156 reaction equation
Cl[C:2]1[C:3]([F:21])=[CH:4][C:5]2[C:6]([CH:20]=1)=[N:7][C:8]1[N:9]([CH3:19])[CH:10]=[C:11]([C:16]([OH:18])=[O:17])[C:12](=[O:15])[C:13]=1[CH:14]=2.[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:25][CH:24]=1.C(O)(=O)C>N1C=CC=CC=1.O>[F:21][C:3]1[C:2]([N:32]2[CH2:31][CH2:30][N:29]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)[CH2:34][CH2:33]2)=[CH:20][C:6]2=[N:7][C:8]3[N:9]([CH3:19])[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

6

Reactant 3

HCID 176Acetic AcidHCID 752601-(4-Fluorophenyl)piperazineHCID 147005548-Chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid

Product 1

HCID 484065RP60556AYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

A suspension of 3.07 g of 8-chloro-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 7.21 g of 4-(4-fluorophenyl)-piperazine in 30 cm3 of pyridine was heated at a temperature around 115° C. for 84 hours. The reaction mixture was concentrated under reduced pressure (20 kPa) at approximately 60° C. The solid obtained was taken up in 50 cm3 of water and 3.5 cm3 of 10% acetic acid were added. The suspension was brought to approximately 100° C. The solidified product was filtered off and washed 3 times with 30 cm3 and 3 times 30 cm3 of warm ethanol. After recrystallizing twice from 65 cm3 of dimethylformamide on each occasion, 2.82 g of 7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid were obtained in the form of a yellow solid melting at about 318-319° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure (20 kPa) at approximately 60° C
  2. customThe solid obtained
  3. customwas brought to approximately 100° C
  4. filtrationThe solidified product was filtered off
  5. washwashed 3 times with 30 cm3 and 3 times 30 cm3 of warm ethanol
  6. customAfter recrystallizing twice from 65 cm3 of dimethylformamide on each occasion

Sources & evidence

ORD record
ord-f0ae10760f564fe8866a6e911339a3fe
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

Loading…