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

HRID 1428703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428703
[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]

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-95cfa4ebf2d040a3a903519252f2b278
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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