Acetic Acid → 4-(5-Fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-1-(2-(trifluoromethyl)quinolin-5-ylimino)-pentan-2-ol

HRID 2215430Notes

Reaction equation

HRID 2215430 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2.[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:35][CH3:36])=[C:21]([C:23]([CH3:34])([CH3:33])[CH2:24][C:25]([OH:32])([C:28]([F:31])([F:30])[F:29])[CH:26]=O)[CH:22]=1.C(O)(=O)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([O:35][CH3:36])=[C:21]([C:23]([CH3:33])([CH3:34])[CH2:24][C:25]([C:28]([F:30])([F:31])[F:29])([OH:32])[CH:26]=[N:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:13])[F:14])=[N:7]3)[CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 21226206Ethyl acetate hexaneHCID 219487892-(Trifluoromethyl)quinolin-5-amine

Product 1

HCID 219488744-(5-Fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-1-(2-(trifluoromethyl)quinolin-5-ylimino)-pentan-2-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 250 mg (1.18 mmol) of 5-amino-2-(trifluoromethyl)quinoline is reacted with 438 mg (1.42 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal and 1.30 ml of concentrated acetic acid in 20 ml of toluene. After chromatography on silica gel with hexane-ethyl acetate (0–100%), 500 mg (84% of theory) of the product is obtained.

Sources & evidence

ORD record
ord-faf1b0379ca740448ef3f3b3fe74f607
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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