Triethylamine → 2-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C:15]1([CH3:33])[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=[C:23]([C:29]([F:32])([F:31])[F:30])[N:22]=2)[CH:16]=1.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:14])[C:11]([NH:28][CH2:27][C:26]2[C:21]([C:17]3[CH:16]=[C:15]([CH3:33])[CH:20]=[CH:19][CH:18]=3)=[N:22][C:23]([C:29]([F:32])([F:30])[F:31])=[CH:24][CH:25]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2-(3-chloro-4-cyanophenyl)propanoic acid (95 mg, 0.454 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (121 mg, 0.454 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (131 mg, 0.681 mmol), 1-hydroxybenzotriazole (92 mg, 0.681 mmol) and triethylamine (0.16 mL, 1.135 mmol). The reaction mixture was stirred for 15 h at room temperature. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-chloro-4-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (182 mg) was obtained as 88% yield.
Workup
- washwashed with water and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customThe filtrate removed in vacuo
- customThe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-91607e5b2b1948aeafad9c02a777f2ed
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937092B2
Reaction notes
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