Triethylamine → (1-Cyclopropyl-propyl)-[4-(4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine

HRID 1831533ノート

反応式

HRID 1831533 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]([N+:16]([O-:18])=[O:17])[C:11](=O)[N:12]=[CH:13][CH:14]=2)=[C:5]([CH3:19])[CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.CCN(CC)CC.Cl.[CH:49]1([CH:52]([NH2:55])[CH2:53][CH3:54])[CH2:51][CH2:50]1>>[CH:49]1([CH:52]([NH:55][C:11]2[C:10]([N+:16]([O-:18])=[O:17])=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:19])[CH:14]=[CH:13][N:12]=2)[CH2:53][CH3:54])[CH2:51][CH2:50]1

参加物

6

反応物 5

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 67749Trifluoromethanesulfonic anhydrideHCID 187699371-Cyclopropylpropan-1-amine hydrochlorideHCID 220520854-(4-methoxy-2-methyl-phenyl)-3-nitro-3H-pyridin-2-one

生成物 1

HCID 22052063(1-Cyclopropyl-propyl)-[4-(4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine収率 54%

反応条件

温度
-78 °C

実験手順

To a solution of 4-(4-methoxy-2-methyl-phenyl)-3-nitro-3H-pyridin-2-one (0.321 g, 1.23 mmol) CH2Cl2 (13 mL), was added Na2CO3 (0.317 g, 3.02 mmol). The reaction was cooled to −78° C., and trifluoromethanesulfonic anhydride (617 μL, 3.65 mmol) was added dropwise. After the addition, the reaction stirred for 15 min at −78° C., then warmed to 0° C. for 1 h. The reaction mixture was filtered and the collected solid was washed with CHCl3. The filtrate was concentrated in vacuo and dissolved in toluene (20 mL) followed by Et3N (343 μL, 2.4 mmol) and 1-cyclopropyl propyl amine HCl (0.331 g, 2.4 mmol), and heated at 130° C. overnight. The reaction was cooled and poured onto ice/H2O. The mixture was extracted with CH2Cl2, washed with H2O, brine, dried Na2SO4, filtered, and concentrated in vacuo. Purification using flash chromatography (10% EtOAc/Hexane) gave 0.220 g (54%) of (1-cyclopropyl-propyl)-[4-(4-methoxy-2-methyl-phenyl)-3-nitro-pyridin-2-yl]-amine: MS(AP) m/z 342.1 [(M+H)+, 100]. The purified intermediate was used in the following step.

後処理

  1. additionAfter the addition
  2. temperaturewarmed to 0° C. for 1 h
  3. filtrationThe reaction mixture was filtered
  4. washthe collected solid was washed with CHCl3
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutiondissolved in toluene (20 mL)
  7. temperatureheated at 130° C. overnight
  8. temperatureThe reaction was cooled
  9. additionpoured onto ice/H2O
  10. extractionThe mixture was extracted with CH2Cl2
  11. washwashed with H2O, brine, dried Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customPurification

出典と根拠

ORDレコード
ord-8b12c8cd22d94da7aa1c43329e4e0ee2
出典データセット
uspto-grants-2006_06
特許番号
US07067658B2

反応ノート

読み込み中…