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

HRID 344918Notes

Reaction equation

HRID 344918 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18](F)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2].[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[CH:29]1[CH2:34][NH:33][CH2:32][CH2:31][NH:30]1>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:23])[C:8]2[CH:9]=[C:10]3[CH:20]=[C:19]([F:21])[C:18]([N:33]4[CH2:32][CH2:31][NH:30][CH:29]([C:25]5[S:24][CH:28]=[CH:27][CH:26]=5)[CH2:34]4)=[CH:17][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 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 53657399(RS)-3-Ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl]-1,4-dihydrobenzo[b][1,8]naphthyridineYield 96.5%

Procedure

(RS)-3-Ethoxycarbonyl-7-fluoro-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-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.59 g) and (RS)-2-(2-thienyl)piperazine (1.02 g). (RS)-3-Ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-8-[3-(2-thienyl)-1-piperazinyl ]-1,4-dihydrobenzo[b][1,8]naphthyridine (2.25 g) is obtained in the form of a yellow solid, m.p. 228° C.

Workup

  1. custom(RS)-3-Ethoxycarbonyl-7-fluoro-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-2fa0f3d22a274c37a07a02de28f77cd1
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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