4-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal → 4-(5-Fluoro-2-methoxyphenyl)-1-(2-(morpholin-4-ylmethyl)quinolin-5-ylimino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

HRID 2215465Notes

Reaction equation

HRID 2215465 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]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[N:7]2.[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:38][CH3:39])=[C:24]([C:26]([CH3:37])([CH3:36])[CH2:27][C:28]([OH:35])([C:31]([F:34])([F:33])[F:32])[CH:29]=O)[CH:25]=1>C(O)(=O)C.C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[CH:22][C:23]([O:38][CH3:39])=[C:24]([C:26]([CH3:36])([CH3:37])[CH2:27][C:28]([C:31]([F:33])([F:34])[F:32])([OH:35])[CH:29]=[N:1][C:2]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)=[N:7]3)[CH:25]=1

Participants

5

Reactant 2

HCID 115731224-(5-Fluoro-2-methoxy-phenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalHCID 219488345-Amino-2-(morpholin-4-ylmethyl)quinoline

Product 1

HCID 219489054-(5-Fluoro-2-methoxyphenyl)-1-(2-(morpholin-4-ylmethyl)quinolin-5-ylimino)-4-methyl-2-(trifluoromethyl)pentan-2-ol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 180 mg (0.74 mmol) of 5-amino-2-(morpholin-4-ylmethyl)quinoline is reacted with 274 mg (0.89 mmol) of 4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal in 0.8 ml of concentrated acetic acid and 20 ml of toluene. After purification on silica gel with hexane-ethyl acetate (0–100%), 220 mg (56% of theory) of the product is obtained.

Workup

  1. customAfter purification on silica gel with hexane-ethyl acetate (0–100%), 220 mg (56% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-7b4feaf8419841d5966714ee0bfe4be5
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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