1-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → Ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate

HRID 1266170Notes

Reaction equation

HRID 1266170 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[CH2:28]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[C:29]1[O:33][CH:32]=[CH:31][CH:30]=1>CS(C)=O.C(N(CC)CC)C>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[C:14]([F:20])=[C:15]([N:37]5[CH2:38][CH2:39][N:34]([CH2:28][C:29]6[O:33][CH:32]=[CH:31][CH:30]=6)[CH2:35][CH2:36]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 185491641-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 185491724-Furfurylpiperazine hydrochloride

Product 1

HCID 18549171Ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylateYield 59.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8471TriethylamineSolvent

Procedure

Ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 3, but from 1.8 g of ethyl 1-cyclopropyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo-[b][1,8]naphthyridine-3-carboxylate and 4.8 g of 4-furfurylpiperazine hydrochloride in 30 cm3 of dimethyl sulphoxide and 5.2 cm3 of triethylamine. 1.5 g of ethyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate were obtained in the form of a yellow-brown solid melting at about 125-128° C., which solid was used without additional purification in the subsequent stages.

Workup

  1. customEthyl 1-cyclopropyl-7,9-difluoro-8-(4-furfurylpiperazin-1-yl)-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylate was prepared under the conditions of Example 3

Sources & evidence

ORD record
ord-b08bd07929f141729450147fe50b774a
Source dataset
uspto-grants-2003_04
Patent number
US06548506B2

Reaction notes

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