HCID 57636446, compound → HCID 57636448, compound

HRID 2110270Notes

Reaction equation

HRID 2110270 reaction equation
[CH:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[NH:7][N:6]=1)([CH3:3])[CH3:2]>CCO>[CH:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[NH:7][N:6]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 57636446HCID 57636446, compound

Product 1

HCID 57636448HCID 57636448, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

Isopropyl-(6-nitro-1H-indazol-3-yl)-amine (0.070 g, 0.318 mmol) and SnCL2.2H2O (0.365 g, 1.62 mmol) were added to 5 mL EtOH, and the reaction mixture was heated to 78° C. and stirred for four hours. The reaction mixture was cooled and concentrated under reduced pressure. The resulting oil was dissolved in 5 mL EtOH and the solution was treated with 5 mL saturated aqueous NaHCO3. The resulting solid was removed by filtration, and the filtrate was washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (EtOAc/hexanes 0-100%) to give 0.036 g of N*3*-Isopropyl-1H-indazole-3,6-diamine, MS (M+H)=219.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting oil was dissolved in 5 mL EtOH
  4. additionthe solution was treated with 5 mL saturated aqueous NaHCO3
  5. customThe resulting solid was removed by filtration
  6. washthe filtrate was washed with saturated aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was chromatographed through silica gel (EtOAc/hexanes 0-100%)

Sources & evidence

ORD record
ord-a717c0c0feb0478c9d2b452e0aa4d4ef
Source dataset
uspto-grants-2009_04
Patent number
US07517901B2

Reaction notes

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