4-(3-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → 2-Amino-5-{[6-chloro-4,4-dimethyl-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-8-fluoro-quinoline

HRID 1444528Notes

Reaction equation

HRID 1444528 reaction equation
[Cl:1][C:2]1[C:3]([O:20][CH3:21])=[C:4]([C:8]([CH3:19])([CH3:18])[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]2[C:25](=[C:26]([F:34])[CH:27]=[CH:28][C:29]=2[NH2:33])[N:24]=1>>[NH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[C:26]([F:34])[CH:27]=[CH:28][C:29]=2[NH:33][CH:11]2[C:5]3[C:4](=[C:3]([O:20][CH3:21])[C:2]([Cl:1])=[CH:7][CH:6]=3)[C:8]([CH3:18])([CH3:19])[CH2:9][C:10]2([OH:17])[C:13]([F:14])([F:16])[F:15])[N:24]=1

Participants

3

Reactant 2

HCID 179891374-(3-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 179891522,5-Diamino-8-fluoroquinoline

Product 1

HCID 686807122-Amino-5-{[6-chloro-4,4-dimethyl-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-8-fluoro-quinoline

Procedure

Analogously to Example 10, the corresponding imine is produced starting from 250 g of 4-(3-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanal and 137 mg of 2,5-diamino-8-fluoroquinoline. The title compound is obtained analogously to Example 3 by reaction of the imine that is formed with 1.0 ml of titanium tetrachloride solution (1 M in dichloromethane).

Sources & evidence

ORD record
ord-88c83487969d44fab73064c61fcff5ea
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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