Triethylamine → 2-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428793
[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]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 225698632-(4-Cyanophenyl)propanoic acidHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Produkt 1

HCID 866802292-(4-Cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04bf24511ccb4a0f82b6c31ecb1b1257
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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