Triethylamine → 1-(Isoquinolin-1-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea

HRID 571993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571993
[C:1]1([NH:11][C:12](=[O:20])OC2C=CC=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[CH3:21][CH:22]1[CH2:27][CH2:26][N:25]([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)[CH2:24][CH2:23]1.C(N(CC)CC)C>CS(C)=O.O>[C:1]1([NH:11][C:12]([NH:35][CH2:34][C:33]2[C:28]([N:25]3[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]3)=[N:29][C:30]([C:36]([F:39])([F:37])[F:38])=[CH:31][CH:32]=2)=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86676325Phenyl isoquinolin-1-ylcarbamate

Produkt 1

HCID 712369611-(Isoquinolin-1-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)ureaAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Phenyl isoquinolin-1-ylcarbamate (80 mg, 0.30 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (87 mg, 0.32 mmol) was dissolved in dimethyl sulfoxide. Then triethylamine (0.08 mL, 0.61 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-(isoquinolin-1-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea (example compound 20) (46 mg, 34%).

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-0669b994b64d4f7b97431cb7bff4e538
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029378B2

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