Acetic Acid → HCID 21948889, compound

HRID 2215421Notes

Reaction equation

HRID 2215421 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[F:12][C:13]1[CH:14]=[CH:15][C:16]([O:31][CH3:32])=[C:17]([C:19]2([CH2:22][C:23]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH:24]=O)[CH2:21][CH2:20]2)[CH:18]=1.C(O)(=O)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[N:7]1[C:8]2[C:3](=[C:2]([N:1]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])([OH:30])[CH2:22][C:19]3([C:17]4[CH:18]=[C:13]([F:12])[CH:14]=[CH:15][C:16]=4[O:31][CH3:32])[CH2:21][CH2:20]3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 119115-AminoquinolineHCID 21226206Ethyl acetate hexaneHCID 219489133-[1-(5-Fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanal

Product 1

HCID 21948889HCID 21948889, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Analogously to Example 37, 362 mg (2.5 mmol) of 5-aminoquinoline is reacted with 640 mg (2.09 mmol) of 3-[1-(5-fluoro-2-methoxyphenyl)cycloprop-1-yl]-2-hydroxy-2-(trifluoromethyl)propanal and 2.80 ml of concentrated acetic acid in 19 ml of toluene. After 6 hours, the chromatography is carried out on silica gel with hexane-ethyl acetate (0–100%), and 810 mg (90% of theory) of the product is obtained.

Workup

  1. customis obtained

Sources & evidence

ORD record
ord-380dfc66285b4a869275e3601b82e393
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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