1-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → (RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344916Notes

Reaction equation

HRID 344916 reaction equation
[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15](F)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:3][CH2:2]1.[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[CH:31]1[CH2:36][NH:35][CH2:34][CH2:33][NH:32]1>>[CH:1]1([N:4]2[C:13]3[N:12]=[C:11]4[CH:14]=[C:15]([N:35]5[CH2:34][CH2:33][NH:32][CH:31]([C:27]6[O:26][CH:30]=[CH:29][CH:28]=6)[CH2:36]5)[C:16]([F:18])=[CH:17][C:10]4=[CH:9][C:8]=3[C:7](=[O:20])[C:6]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5]2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 148533401-Cyclopropyl-3-ethoxycarbonyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 167407772-(Furan-2-yl)piperazine

Product 1

HCID 54566174(RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 89.5%

Procedure

(RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39, but starting with 1-cyclopropyl-7,8-difluoro-3-ethoxycarbonyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.05 g) and (RS)-2-(2-furyl)piperazine (0.6 g). (RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.3 g) is obtained in the form of a yellow solid, m.p. 182° C.

Workup

  1. custom(RS)-1-Cyclopropyl-3-ethoxycarbonyl-7-fluoro-8-[3-(2-furyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39

Sources & evidence

ORD record
ord-654d519a2a124b2aa2c94ffeddf1cafd
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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