5-amino-8-fluoroquinolin-2(1H)-one → 8-fluoro-5-{[4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one

HRID 1362494Notes

Reaction equation

HRID 1362494 reaction equation
[F:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([CH:8]([CH2:18][CH3:19])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=O)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[CH:32]=[CH:31][C:30]([F:33])=[C:29]2[C:24]=1[CH:25]=[CH:26][C:27](=[O:34])[NH:28]2>>[F:33][C:30]1[CH:31]=[CH:32][C:23]([N:22]=[CH:11][C:10]([OH:17])([C:13]([F:14])([F:15])[F:16])[CH2:9][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[O:20][CH3:21])[CH2:18][CH3:19])=[C:24]2[C:29]=1[NH:28][C:27](=[O:34])[CH:26]=[CH:25]2

Participants

3

Reactant 2

HCID 179891895-amino-8-fluoroquinolin-2(1H)-oneHCID 866153234-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal

Product 1

HCID 669694808-fluoro-5-{[4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one

Procedure

In the same way as in Example 29, 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal and 5-amino-8-fluoroquinolin-2(1H)-one are condensed to give 8-fluoro-5-{[4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one. Reaction with 1 M boron tribromide solution after column chromatography on silica gel (hexane/ethyl acetate 33-100%) and preparative HPLC yield not only the desired product but also the methyl ether cleaved compounds Example 35 and 44.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-47b5f772f54c4502b4c9a890db40e04d
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

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