Dimethylformamide → 3-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine

HRID 335087

Reaktionsgleichung

Reaktionsgleichung von HRID 335087
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[S:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C.Br[CH:27]1[CH2:32][CH2:31][CH2:30][CH:29]=[CH:28]1>O>[CH:32]1([O:14][C:13]2[C:8]([NH:7][C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:31][CH2:30][CH2:29][CH:28]=[CH:27]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 1370573-BromocyclohexeneHCID 104656162-(4-Methylthiazol-2-ylamino)pyridin-3-ol

Produkt 1

HCID 247659313-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amineAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

2-(4-Methylthiazol-2-ylamino)pyridin-3-ol (0.250 g, 1.21 mmol) and Cs2CO3 (1.18 g, 3.62 mmol) were added to DMF (3 mL). 3-Bromocyclohex-1-ene (0.216 g, 1.21 mmol) was added, and the reaction mixture was stirred for 3 hours. Water was added and the reaction mixture was extracted with ether. The organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography provide 3-(cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amine (0.130 g=37.5%). 1H NMR (d6-DMSO) δ 9.53 (s, 1H), 7.85 (dd, 1H), 7.41 (d, 1H), 6.90 (dd, 1H), 6.58 (s, 1H), 6.00 (m, 1H), 6.88 (m, 1H), 6.88 (m, 1H), 4.99 (m, 1H), 2.24 (s, 3H), 2.05 (m, 2H), 1.87 (m, 3H), 1.62 (m, 1H); Mass spectrum (apci) m/z=288.0 (M+H).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ether
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8ab4f2aa02cc4a7f84a51d714aa09729
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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