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

HRID 1443260Notes

Reaction equation

HRID 1443260 reaction equation
[F: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.NC1C=CC(F)=C2C=1C=CC(=O)N2.[NH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[C:39]([F:47])[CH:40]=[CH:41][C:42]=2[NH2:46])[N:37]=1>[Ti](Cl)(Cl)(Cl)Cl>[NH2:35][C:36]1[CH:45]=[CH:44][C:43]2[C:38](=[C:39]([F:47])[CH:40]=[CH:41][C:42]=2[NH:46][CH:11]2[C:5]3[C:4](=[C:3]([O:20][CH3:21])[C:2]([F:1])=[CH:7][CH:6]=3)[C:8]([CH3:19])([CH3:18])[CH2:9][C:10]2([OH:17])[C:13]([F:16])([F:14])[F:15])[N:37]=1

Participants

5

Reactant 3

HCID 179890864-(3-Fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 179891522,5-Diamino-8-fluoroquinolineHCID 179891895-amino-8-fluoroquinolin-2(1H)-one

Product 1

HCID 686798322-Amino-5-{[4,4-dimethyl-6-fluoro-2-hydroxy-5-methoxy-2-(trifluoromethyl)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}-8-fluoro-quinoline

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

Analogously to Example 10, a mixture of the corresponding imines is produced starting from 237 g of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 137 mg of a mixture that consists of 5-amino-8-fluoroquinolin-2(1H)-one and 2,5-diamino-8-fluoroquinoline. Analogously to Example 3, the mixture of imines with 2.5 ml of titanium tetrachloride solution (1 M in dichloromethane) is reacted, and the two title compounds are obtained after chromatography on silica gel.

Workup

  1. customis produced
  2. customis reacted
  3. customthe two title compounds are obtained after chromatography on silica gel

Sources & evidence

ORD record
ord-86d770cafe674d60907599032e4d0e79
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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