3-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine → 8-(3-Cyclopropylamino-1-azetidinyl)3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 743668Notes

Reaction equation

HRID 743668 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.[CH:26]1([NH:29][CH:30]2[CH2:33][NH:32][CH2:31]2)[CH2:28][CH2:27]1>>[CH:26]1([NH:29][CH:30]2[CH2:33][N:32]([C:18]3[C:19]([F:21])=[CH:20][C:10]4[C:11]([CH:17]=3)=[N:12][C:13]3[N:14]([CH3:16])[CH:15]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:7](=[O:23])[C:8]=3[CH:9]=4)[CH2:31]2)[CH2:28][CH2:27]1

Participants

3

Reactant 2

HCID 98399873-Ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineHCID 194236593-(Cyclopropylamino)azetidine dihydrochloride

Product 1

HCID 194236458-(3-Cyclopropylamino-1-azetidinyl)3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridineYield 72.2%

Procedure

8-(3-Cyclopropylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 15, but starting with 1.45 g of 3-ethoxycarbonyl-7,8-difluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine and 1.7 g of 3-(cyclopropylamino)azetidine dihydrochloride. 1.35 g of 8-(3-cyclopropylamino-1-azetidinyl)3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 221° C. and then 245° C.

Workup

  1. custom8-(3-Cyclopropylamino-1-azetidinyl)-3-ethoxycarbonyl-7-fluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions of Example 15

Sources & evidence

ORD record
ord-bfc70fbfb18343319540a934ef5622b6
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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