Triethylamine → 1-((2-(Cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(isoquinolin-4-yl)urea

HRID 571991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571991
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][C:12](=[O:20])OC2C=CC=CC=2)=[CH:3][N:2]=1.[CH:21]1([S:27][C:28]2[C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=[C:30]([C:36]([F:39])([F:38])[F:37])[N:29]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>CS(C)=O.O>[CH:21]1([S:27][C:28]2[C:33]([CH2:34][NH:35][C:12]([NH:11][C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=[N:2][CH:3]=3)=[O:20])=[CH:32][CH:31]=[C:30]([C:36]([F:38])([F:39])[F:37])[N:29]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 58442686Phenyl isoquinolin-4-ylcarbamateHCID 67300770(2-(Cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methanamine

Produkt 1

HCID 712370421-((2-(Cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(isoquinolin-4-yl)ureaAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Phenyl isoquinolin-4-ylcarbamate (68 mg, 0.26 mmol) and (2-(cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methanamine (78 mg, 0.27 mmol) were dissolved in dimethyl sulfoxide. Then triethylamine (0.08 mL, 0.52 mmol) was added to it. The mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give 1-((2-(cyclohexylthio)-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-(isoquinolin-4-yl)urea (example compound 19) (16 mg, 14%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0424043986f04263bd89f08f9fd1fbad
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029378B2

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