Potassium Carbonate → 3-Ethoxycarbonyl-7,9-difluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine

HRID 344922Notes

Reaction equation

HRID 344922 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].Cl.Cl.[OH:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[K+].[K+]>>[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:31]4[CH2:32][CH2:33][N:28]([OH:27])[CH2:29][CH2:30]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

4

Reactant 3

HCID 11430Potassium CarbonateHCID 12463394Piperazin-1-ol dihydrochlorideHCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

Product 1

HCID 545271483-Ethoxycarbonyl-7,9-difluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridineYield 59.2%

Procedure

3-Ethoxycarbonyl-7,9-difluoro-8-(4-hydroxy-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 (1.9 g), 1-hydroxypiperazine dihydrochloride (1 g) and potassium carbonate (1.6 g). 3-Ethoxycarbonyl-7,9-difluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine (1.4 g) is obtained in the form of a yellow solid, m.p. 255°-258° C.

Workup

  1. custom3-Ethoxycarbonyl-7,9-difluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo [b][1,8]naphthyridine was prepared under the conditions of Example 39

Sources & evidence

ORD record
ord-af4dfd9d8b9c4b5cb5c5ceed7b638eaa
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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