2-(4-methoxyphenyl)piperazine → (RS)-3-Ethoxycarbonyl-1-ethyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344904Notes

Reaction equation

HRID 344904 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:21]=[C:20]([F:22])[C:19](F)=[CH:18][C:11]3=[N:12][C:13]=2[N:14]([CH2:16][CH3:17])[CH:15]=1)=[O:5])[CH3:2].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]2[CH2:38][NH:37][CH2:36][CH2:35][NH:34]2)=[CH:29][CH:28]=1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:21]=[C:20]([F:22])[C:19]([N:37]4[CH2:36][CH2:35][NH:34][CH:33]([C:30]5[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=5)[CH2:38]4)=[CH:18][C:11]3=[N:12][C:13]=2[N:14]([CH2:16][CH3:17])[CH:15]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 27717532-(4-methoxyphenyl)piperazineHCID 194236943-Ethoxycarbonyl-7,8-difluoro-1-ethyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54178707(RS)-3-Ethoxycarbonyl-1-ethyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 72.8%

Procedure

(RS)-3-Ethoxycarbonyl-1-ethyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 33, but starting with 3-ethoxycarbonyl-1-ethyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine (1.99 g) and (RS)-2-(4-methoxyphenyl)piperazine (2.3 g). (RS)-3-Ethoxycarbonyl-1-ethyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (2.2 g) is obtained in the form of a beige solid, m.p. 210°-212° c.

Workup

  1. custom(RS)-3-Ethoxycarbonyl-1-ethyl-7-fluoro-8-[3-(4-methoxyphenyl)-1-piperazinyl]-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 33

Sources & evidence

ORD record
ord-f54b493cb68f40acb6e2f1140abfd8f3
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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