Cesium carbonate → 1-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

HRID 517955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517955
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[C:11]3[N:16]=[N:17][N:18]([CH3:19])[C:10]=3[CH:9]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].CS(O[CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=2)[CH2:32][CH2:31]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C(OCC)(=O)C>[CH3:19][N:18]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][CH2:29][CH:30]4[CH2:35][CH2:34][N:33]([C:36]5[CH:41]=[C:40]([CH3:42])[CH:39]=[CH:38][N:37]=5)[CH2:32][CH2:31]4)=[C:3]([C:20]([F:23])([F:22])[F:21])[CH:4]=3)[N:13]=[C:12]([C:14]#[N:15])[C:11]=2[N:16]=[N:17]1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 86673349(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonateHCID 1363523116-(4-hydroxy-3-(trifluoromethyl)-phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Produkt 1

HCID 672944701-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-(4-Hydroxy-3-(trifluoromethyl)phenyl)-1-methyl-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile (0.626 mmol, 0.2 g), (1-(4-methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonate (0.752 mmol, 0.214 g), cesium carbonate (0.940 mmol, 0.306 g) and tetrabutylammonium iodide (0.313 mmol, 0.116 g) were stirred in DMF (1 ml) at 50° C. overnight. The reaction mixture was diluted with ethyl acetate, washed with water and dried over Na2SO4. The resulting residue was triturated with ether and filtered. The solid was sonicated in methanol, filtered and dried to afford 1-methyl-6-(4-((1-(4-methylpyridin-2-yl)piperidin-4-yl)methoxy)-3-(trifluoromethyl)phenyl)-1H-[1,2,3]triazolo[4,5-c]pyridine-4-carbonitrile. (134 mg)

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. customThe resulting residue was triturated with ether
  4. filtrationfiltered
  5. customThe solid was sonicated in methanol
  6. filtrationfiltered
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0062adda6d6a425b83fd8cd04bbef92a
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115126B2

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