4-(Pyrrolidin-3-yl)pyridine → 1-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-[3-(4-pyridinyl)-1-pyrrolidinyl]-1,8-naphthyridine-3-carboxylic acid

HRID 54494Notes

Reaction equation

HRID 54494 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])=[CH:4][C:3]=1[F:24].[NH:25]1[CH2:29][CH2:28][CH:27]([C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)[CH2:26]1>>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[N:9]1[C:10]2[C:5](=[CH:4][C:3]([F:24])=[C:2]([N:25]3[CH2:29][CH2:28][CH:27]([C:30]4[CH:31]=[CH:32][N:33]=[CH:34][CH:35]=4)[CH2:26]3)[N:11]=2)[C:6](=[O:23])[C:7]([C:20]([OH:22])=[O:21])=[CH:8]1

Participants

3

Reactant 2

HCID 49931054-(Pyrrolidin-3-yl)pyridineHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Product 1

HCID 152312971-(2,4-Difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-7-[3-(4-pyridinyl)-1-pyrrolidinyl]-1,8-naphthyridine-3-carboxylic acidYield 56%

Procedure

Starting from 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (0.51 g, 1.5 mmol) and 4-(3-pyrrolidinyl) pyridine, a procedure analogous to that given in Example 1, provided the title compound (0.39 g, 56%) as an off-white solid, mp 253°-255° C. (dec).

Sources & evidence

ORD record
ord-06373090141d47da9b7d333c53889b3b
Source dataset
uspto-grants-1997_04
Patent number
US05622966

Reaction notes

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