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Hydrochloric Acid → (E)-2-[2-(1H-indazol-3-yl)vinyl]-4-methoxy-5-[3-(morpholin-4-yl)propyloxy]phenylamine

HRID 1821427
ノート
印刷プレビュー

反応式

HRID 1821427 の反応式
[CH3:1][O:2][C:3]1[C:4]([O:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:5][C:6]([N+:20]([O-])=O)=[C:7](/[CH:9]=[CH:10]/[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)[CH:8]=1.[Sn].Cl.[OH-].[Na+]>C(O)C>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](/[CH:10]=[CH:9]/[C:7]2[CH:8]=[C:3]([O:2][CH3:1])[C:4]([O:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:5][C:6]=2[NH2:20])=[N:12]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 68998380(E)-3-{2-[5-methoxy-4-[3-(morpholin-4-yl)propyloxy]-2-nitrophenyl]vinyl}-1H-indazole

生成物 1

HCID 68999047(E)-2-[2-(1H-indazol-3-yl)vinyl]-4-methoxy-5-[3-(morpholin-4-yl)propyloxy]phenylamine収率 89%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
40 °C

実験手順

(E)-3-{2-[5-methoxy-4-(3-(morpholin-4-yl) propyloxy)-2-nitrophenyl]vinyl}-1H-indazole (0.39 g, 0.89 mmol) obtained in Step 2 was dissolved in ethanol (3.0 mL), and the solution was added with tin (0.22 g, 1.9 mmol) and concentrated hydrochloric acid (1.5 mL) under ice-cooling, followed by stirring at 40° C. for 6 hours. To the reaction mixture under ice-cooling, 6 mol/L aqueous sodium hydroxide solution was added to neutralize the mixture. Then, the mixture was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1) to obtain (E)-2-[2-(1H-indazol-3-yl)vinyl]-4-methoxy-5-[3-(morpholin-4-yl)propyloxy]phenylamine (0.32 g, 89%).

後処理

  1. temperaturecooling
  2. temperatureTo the reaction mixture under ice-cooling
  3. filtrationThen, the mixture was filtered
  4. additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe filtrate was purified by silica gel column chromatography (chloroform to chloroform/methanol=9/1)

出典と根拠

ORDレコード
ord-3e5f3caf0e6a4909b2771ac039d45641
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07605272B2

反応ノート

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