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

HRID 335087

Reaction equation

HRID 335087 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 247659313-(Cyclohex-2-enyloxy)-N-(4-methylthiazol-2-yl)pyridin-2-amineYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8ab4f2aa02cc4a7f84a51d714aa09729
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Linked notes

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