3-Amino-4-cyclopropyl-but-2-enoic acid ethyl ester → 2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-nicotinic acid ethyl ester

HRID 890488Notes

Reaction equation

HRID 890488 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]=[C:6]([NH2:11])[CH2:7][CH:8]1[CH2:10][CH2:9]1)[CH3:2].[F:13][C:14]([F:32])([F:31])/[C:15](/O)=[CH:16]/[C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)=O>C(#N)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[C:15]([C:14]([F:13])([F:32])[F:31])=[CH:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:27])([F:28])[F:29])=[CH:21][CH:20]=2)=[N:11][C:6]=1[CH2:7][CH:8]1[CH2:9][CH2:10]1)[CH3:2]

Participants

4

Reactant 2

HCID 670720963-Amino-4-cyclopropyl-but-2-enoic acid ethyl esterHCID 178520888HCID 178520888, compound

Product 1

HCID 865977852-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-nicotinic acid ethyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Amino-4-cyclopropyl-but-2-enoic acid ethyl ester (231 mg, 1.4 mmol) was added to a solution of (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethoxy-phenyl)-but-2-en-1-one (819 mg, 2.7 mmol; example 16 a]) in acetonitrile (2.7 ml). The mixture was heated under reflux conditions for 12 h, the solvent was removed under reduced pressure and the residue purified by flash chromatography (silica gel, heptane/AcOEt) to give 242 mg (0.56 mmol, 41%) of the title compound as yellow oil.

Workup

  1. temperatureThe mixture was heated under reflux conditions for 12 h
  2. customthe solvent was removed under reduced pressure
  3. customthe residue purified by flash chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-a0a3dd88bc8a4d25a52e8a865ed8df55
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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