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

HRID 344917Notes

Reaction equation

HRID 344917 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].[O: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[O: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 167407772-(Furan-2-yl)piperazineHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 54195109(RS)-3-Ethoxycarbonyl-7,9-difluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 66.7%

Procedure

(RS)-3-Ethoxycarbonyl-7,9-difluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-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 (1.85 g) and (RS)-2-(2-furyl)piperazine (1 g). After concentration of the combined organic extracts under reduced pressure (20 kPa, approximately 40° C.), the residual solid is recrystallized in ethanol (100 cc). (RS)-3-Ethoxycarbonyl-7,9-difluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (1.72 g) is obtained in the form of a yellow solid, m.p. 208°-210° C.

Workup

  1. custom(RS)-3-Ethoxycarbonyl-7,9-difluoro-8-[3-(2-furyl)-1-piperazinyl]-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 39
  2. customAfter concentration of the combined organic extracts under reduced pressure (20 kPa, approximately 40° C.), the residual solid is recrystallized in ethanol (100 cc)

Sources & evidence

ORD record
ord-90676049fb5c463d908d3cfb7cc0411b
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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