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

HRID 1242525Notes

Reaction equation

HRID 1242525 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

231 mg (1.4 mmol) 3-Amino-4-cyclopropyl-but-2-enoic acid ethyl ester were added to a solution of 819 mg (2.7 mmol) (Z)-4,4,4-trifluoro-3-hydroxy-1-(4-trifluoromethoxy-phenyl)-but-2-en-1-one in 2.7 ml acetonitrile. 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-5a1c717ac56b4385a24f2e306114b8c0
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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