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

HRID 344921Notes

Reaction equation

HRID 344921 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].Cl.Cl.[OH:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[Na+].[Na+]>>[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:30]4[CH2:31][CH2:32][N:27]([OH:26])[CH2:28][CH2:29]4)=[CH:17][C:11]3=[N:12][C:13]=2[N:14]([CH3:16])[CH:15]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 12463394Piperazin-1-ol dihydrochloride

Product 1

HCID 537992403-Ethoxycarbonyl-7-fluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 86.1%

Procedure

3-Ethoxycarbonyl-7-fluoro-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-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8 ]naphthyridine (3 g), 1-hydroxypiperazine dihydrochloride (1.97 g) and sodium carbonate (1.99 g). 3-Ethoxycarbonyl-7-fluoro-8-(4-hydroxy-1-piperazinyl)-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (3.25 g) is obtained in the form of a yellow solid, m.p. 258°-260° C.

Workup

  1. custom3-Ethoxycarbonyl-7-fluoro-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-d97bf273f6d44f4bbb1c99c6e1290a32
Source dataset
uspto-grants-1991_10
Patent number
US05053509

Reaction notes

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