3-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanal → HCID 69205241, compound

HRID 2182714Notes

Reaction equation

HRID 2182714 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]2([CH2:11][C:12]([OH:19])([C:15]([F:18])([F:17])[F:16])[CH:13]=O)[CH2:10][CH2:9]2)[CH:7]=1.[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[NH2:36])[N:27]=1)=[O:25]>C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:22][O:23][C:24]([C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[N:36]=[CH:13][C:12]([OH:19])([C:15]([F:18])([F:16])[F:17])[CH2:11][C:8]2([C:6]3[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[O:20][CH3:21])[CH2:10][CH2:9]2)[N:27]=1)=[O:25]

Participants

5

Reactant 2

HCID 219489133-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanalHCID 45089604Methyl 5-aminoquinoline-2-carboxylate

Product 1

HCID 69205241HCID 69205241, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 306 mg (1.2 mmol) of 5-{3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanal is reacted with 170 mg (0.84 mmol) of 5-aminoquinoline-2-carboxylic acid methyl ester in 4.0 ml of concentrated acetic acid and 20 ml of toluene. After working-up and purification on silica gel with hexane-ethyl acetate (0-70%), 204 mg (49% of theory) of the product is obtained.

Workup

  1. custompurification on silica gel with hexane-ethyl acetate (0-70%), 204 mg (49% of theory) of the product
  2. customis obtained

Sources & evidence

ORD record
ord-e2cc2b74d9f944b2ab6dddb688e6386e
Source dataset
uspto-grants-2005_05
Patent number
US06897224B2

Reaction notes

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