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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
Notes
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Reaction equation

HRID 1821427 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents

1
HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-3e5f3caf0e6a4909b2771ac039d45641
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes