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

HRID 335087

反応式

HRID 335087 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8ab4f2aa02cc4a7f84a51d714aa09729
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

関連ノート

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