Ethanol → HCID 18549176, compound

HRID 1266176Notes

Reaction equation

Cl[C:2]1[C:11]([C:12](=[O:23])[C:13](=[CH:19][N:20](C)[CH3:21])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:25])=[C:7]([F:24])[CH:8]=2)[N:3]=1.[F:26][C:27]1[CH:33]=[C:32]([F:34])C=[CH:30][C:28]=1N.C(O)C.N12CCCN=C1CCCCC2>ClC(Cl)Cl>[F:34][C:32]1[CH:33]=[C:27]([F:26])[CH:28]=[CH:30][C:21]=1[N:20]1[C:2]2[N:3]=[C:4]3[CH:5]=[C:6]([F:25])[C:7]([F:24])=[CH:8][C:9]3=[CH:10][C:11]=2[C:12](=[O:23])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19]1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 1-(2,4-difluorophenyl)-7-fluoro-8-[4-(4-fluorophenyl)piperazin-1-yl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was obtained under the conditions of Example 13, but from 3.68 g of ethyl 3-(2-chloro-6,7-difluoro-3-quinolyl)-2-dimethylaminomethylene-3-oxopropionate and 3.87 g of 2,4-difluoroaniline in 40 cm3 of trichloromethane. 50 cm3 of ethanol and 1.5 cm3 of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to the mixture, which was heated at a temperature around 80° C. for approximately 1 hour. After cooling to a temperature around 10° C., the product was filtered off and washed 2 times with 50 cm3 of ethanol and 2 times with 50 cm3 of isopropyl ether. 3.3 g of ethyl 1-(2,4-difluorophenyl)-7,8-difluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow solid melting at approximately 300° C., which solid was used without additional purification in the subsequent stages.

Workup

temperatureAfter cooling to a temperature around 10° C.
filtrationthe product was filtered off
washwashed 2 times with 50 cm3 of ethanol and 2 times with 50 cm3 of isopropyl ether

Sources & evidence

ORD record: ord-1c94e9ddab4a42558517e41fe7082dc8
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548506B2

Reaction notes

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