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

HRID 1821405Notes

Reaction equation

HRID 1821405 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][N:20]=3)=[C:13]([N+:28]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[Sn].Cl.[OH-].[Na+]>C(O)C>[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19](/[CH:18]=[CH:17]/[C:14]2[CH:15]=[CH:16][C:11]([N:8]3[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH2:9]3)=[CH:12][C:13]=2[NH2:28])=[N:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 69000300(E)-3-{2-[4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]vinyl}-1H-indazole

Product 1

HCID 68998362(E)-2-[2-(1H-indazol-3-yl)vinyl]-5-(4-methanesulfonylpiperazin-1-yl)phenylamineYield 52.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(E)-3-{2-[4-(4-methanesulfonylpiperazin-1-yl)-2-nitrophenyl]vinyl}-1H-indazole (0.13 g, 0.29 mmol) obtained in Step 2 was dissolved in ethanol (2.0 mL), and the solution was added with tin (73 mg, 0.62 mmol) and concentrated hydrochloric acid (1.0 mL) under ice-cooling, followed by stirring at 40° C. for 1 hour. 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 residue was triturated in ethyl acetate to obtain (E)-2-[2-(1H-indazol-3-yl)vinyl]-5-(4-methanesulfonylpiperazin-1-yl)phenylamine (0.06 g, 52%).

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 residue was triturated in ethyl acetate

Sources & evidence

ORD record
ord-392f7d40173a44549417b6bf3ee8215b
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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