Triethylamine → 2-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428703Notes

Reaction equation

HRID 1428703 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:42]1([CH3:60])[CH:47]=[CH:46][CH:45]=[C:44]([C:48]2[C:53]([CH2:54][NH2:55])=[CH:52][CH:51]=[C:50]([C:56]([F:59])([F:58])[F:57])[N:49]=2)[CH:43]=1>O1CCOCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:13])[C:10]([NH:55][CH2:54][C:53]2[C:48]([C:44]3[CH:43]=[C:42]([CH3:60])[CH:47]=[CH:46][CH:45]=3)=[N:49][C:50]([C:56]([F:59])([F:57])[F:58])=[CH:51][CH:52]=2)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 532495512-(3-Cyanophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Product 1

HCID 866802072-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(3-cyanophenyl)propanoic acid (85 mg, 48.8 mmol) in 1,4-dioxane was cooled in an ice bath and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (139 mg, 73.2 mmol), N-hydroxybenzotriazole (98 mg, 73.2 mmol), triethylamine (172 μl, 170 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (130 mg, 48.8 mmol), were added consecutively. The reaction mixture was stirred overnight at room temperature. Water was added to the reaction mixture and extracted with dichloromethane. The combined organic extracts were washed successively with saturated NaHCO3 solution, 0.5 N HCl and then water and dried over magnesium sulfate. Evaporation of the solvent followed by column chromatographic purification afforded the 2-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (110 mg, 53%).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic extracts were washed successively with saturated NaHCO3 solution, 0.5 N HCl
  3. dry with materialwater and dried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customfollowed by column chromatographic purification

Sources & evidence

ORD record
ord-95cfa4ebf2d040a3a903519252f2b278
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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