4-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → HCID 21948825, compound

HRID 2054963Notes

Reaction equation

HRID 2054963 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:13])[N:4]=1)[CH3:2].[F:14][C:15]1[CH:16]=[CH:17][C:18]([O:33][CH3:34])=[C:19]([C:21]([CH3:32])([CH3:31])[CH2:22][C:23]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH:24]=O)[CH:20]=1>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N:13]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])([OH:30])[CH2:22][C:21]([C:19]2[CH:20]=[C:15]([F:14])[CH:16]=[CH:17][C:18]=2[O:33][CH3:34])([CH3:31])[CH3:32])[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 21948806HCID 21948806, compound

Product 1

HCID 21948825HCID 21948825, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 334 mg (1.94 mmol) of 2-ethylquinolin-5-ylamine is reacted with 500 mg (1.62 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentanal in 2.20 ml of concentrated acetic acid and 15 ml of toluene. After purification on silica gel with hexane-ethyl acetate (0-100%), 600 mg (80% of theory) of the corresponding imine is obtained.

Workup

  1. customAfter purification on silica gel with hexane-ethyl acetate (0-100%)

Sources & evidence

ORD record
ord-1b97ea8cee28467d97833dcb811d90e7
Source dataset
uspto-grants-2008_02
Patent number
US07329753B2

Reaction notes

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