Water → HCID 69001427, compound

HRID 1821410Notes

Reaction equation

HRID 1821410 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][N:23]=3)=[C:16]([N+:31]([O-])=O)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>C(O)C.[Fe]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][N:23]=3)=[C:16]([NH2:31])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 962Water2×HCID 69000493HCID 69000493, compound

Product 1

HCID 69001427HCID 69001427, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

(E)-4-{4-[2-(1H-indazol-3-yl)vinyl]-3-nitrophenyl}piperazine-1-carboxylic acid tert-butyl ester (0.20 g, 0.45 mmol) obtained in Step 2 was dissolved in ethanol (1.0 mL), and the solution was added with iron (0.50 g, 8.9 mmol) and water (1.0 mL) under ice-cooling, followed by stirring at 40° C. for 1 hour. To the reaction mixture under ice-cooling, water was added and the mixture was neutralized. 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)-4-{3-amino-4-[2-(1H-indazol-3-yl)vinyl]phenyl}piperazine-1-carboxylic acid tert-butyl ester (63 mg, 34%).

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-dd3063daef1543ce927cbc2090838f39
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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