(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide

HRID 1428768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428768
[CH2:1]([S:3]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:23])OC2C=CC=CC=2)=[CH:10][CH:9]=1)(=[O:5])=[O:4])[CH3:2].[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=[C:32]([C:38]([F:41])([F:40])[F:39])[N:31]=2)[CH:25]=1>C(#N)C.CN(C)C1C=CN=CC=1>[C:24]1([CH3:42])[CH:29]=[CH:28][CH:27]=[C:26]([C:30]2[C:35]([CH2:36][NH:37][C:15](=[O:23])[NH:14][C:11]3[CH:10]=[CH:9][C:8]([CH2:7][NH:6][S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:13][CH:12]=3)=[CH:34][CH:33]=[C:32]([C:38]([F:40])([F:39])[F:41])[N:31]=2)[CH:25]=1

Komponenten

5

Edukt 2

HCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86680222Phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate

Produkt 1

HCID 71539386N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of phenyl 4-(ethylsulfonamidomethyl)phenylcarbamate (74 mg, 0.22 mmol) in acetonitrile (3 mL) was added 4-dimethylaminopyridine (27 mg, 0.22 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (59 mg, 0.22 mmol) at room temperature. The reaction mixture was heated to 50° C. for 15 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethylacetate. The organic part was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)ethanesulfonamide (example 82) (50 mg, 45%).

Aufarbeitung

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethylacetate
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-76637c4f762f45209e8f181ff608d86d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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