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Phenyl 4-(methylsulfonamidomethyl)phenylcarbamate → N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

HRID 1428711
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1428711
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)=[CH:9][CH:8]=1)(=[O:4])=[O:3].[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=[C:31]([C:37]([F:40])([F:39])[F:38])[N:30]=2)[CH:24]=1>CN(C)C1C=CN=CC=1>[C:23]1([CH3:41])[CH:28]=[CH:27][CH:26]=[C:25]([C:29]2[C:34]([CH2:35][NH:36][C:14](=[O:22])[NH:13][C:10]3[CH:9]=[CH:8][C:7]([CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:12][CH:11]=3)=[CH:33][CH:32]=[C:31]([C:37]([F:39])([F:38])[F:40])[N:30]=2)[CH:24]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 86679364Phenyl 4-(methylsulfonamidomethyl)phenylcarbamateHCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

Produkt 1

HCID 71539427N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of phenyl 4-(methylsulfonamidomethyl)phenylcarbamate (59 mg, 0.18 mmol) acetonitrile (3 mL) was added 4-dimethylaminopyridine (23 mg, 0.18 mmol) and (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (49 mg, 0.18 mmol) at room temperature. The reaction mixture was heated to 50° C. for 16 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with ethyl acetate. 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 N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%).

Aufarbeitung

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with ethyl acetate
  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 to N-(4-(3-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)ureido)benzyl)methanesulfonamide (example 2) (57 mg, 63%)

Quellen und Nachweise

ORD-Eintrag
ord-826b80af24b242dbbeaa84c6270e1eb7
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08937092B2

Notizen zur Reaktion

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