Triethylamine → 2-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([OH:12])=O)=[CH:5][CH:4]=1)#[N:2].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:35]1([CH3:53])[CH:40]=[CH:39][CH:38]=[C:37]([C:41]2[C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=[C:43]([C:49]([F:52])([F:51])[F:50])[N:42]=2)[CH:36]=1.C(N(CC)CC)C>C(#N)C.C(OC(=O)C)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:13])[C:10]([NH:48][CH2:47][C:46]2[C:41]([C:37]3[CH:36]=[C:35]([CH3:53])[CH:40]=[CH:39][CH:38]=3)=[N:42][C:43]([C:49]([F:52])([F:50])[F:51])=[CH:44][CH:45]=2)=[O:12])=[CH:7][CH:8]=1)#[N:2]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 2-(4-cyanophenyl)propanoic acid (148 mg, 0.85 mmol) in acetonitrile were added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (243 mg, 1.27 mmol), 1-hydroxybenzotriazole (171 mg, 1.27 mmol), (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (247 mg, 0.93 mmol) and triethylamine (0.29 mL, 2.11 mmol). The reaction mixture was stirred for overnight at room temperature. The mixture was diluted with ethylacetate 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-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (311 mg) was obtained as 87% 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-04bf24511ccb4a0f82b6c31ecb1b1257
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937092B2
Reaction notes
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