2-Thiophen-2-yl-piperazine → (RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344920Notes

Reaction equation

HRID 344920 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[CH:30]1[CH2:35][NH:34][CH2:33][CH2:32][NH:31]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:24])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:34]4[CH2:33][CH2:32][NH:31][CH:30]([C:26]5[S:25][CH:29]=[CH:28][CH:27]=5)[CH2:35]4)=[C:17]([F:23])[C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 27717262-Thiophen-2-yl-piperazineHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54467477(RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridineYield 69.4%

Procedure

(RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39, but starting with 3-ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine (1.68 g) and (RS)-2-(2-thienyl)piperazine (1.01 g). (RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridine (1.68 g) is thereby obtained in the form of a yellow solid, m.p. 220° C.

Workup

  1. custom(RS)-3-Ethoxycarbonyl-7,9-difluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39

Sources & evidence

ORD record
ord-2c09f7ea4afa439fbc151405a0efeeef
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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