N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide → 6-Amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide

HRID 1621031

Reaction equation

HRID 1621031 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[O:13][C:14]3[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:15]=3[CH:16]=1)=[O:11])[CH2:2]2>[Sn](Cl)Cl.CN(C=O)C>[NH2:21][C:19]1[CH:18]=[CH:17][C:15]2[CH:16]=[C:12]([C:10]([NH:9][C@@H:3]3[CH:4]4[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]4)[CH2:2]3)=[O:11])[O:13][C:14]=2[CH:20]=1

Participants

4

Reactant 1

HCID 59341358N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide

Product 1

HCID 593414346-Amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-2-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24479Stannous ChlorideSolvent

Procedure

1.55 g (4.92 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-nitro-1-benzofuran-2-carboxamide are dissolved in 15 ml of 2 M tin(II) chloride solution in DMF and stirred at room temperature overnight. Dowex 50WX2-200 ion exchanger resin is added and, within 1 h, the mixture is concentrated in a rotary evaporator. The resin is washed successively with water, DMF, methanol, dichloromethane, methanol and 10% triethylamine in methanol. The product fraction is concentrated and chromatographed on silica gel (mobile phase: dichloromethane/methanol/triethylamine). Concentration in vacuo results in 642.8 mg (45.8% of theory) of the title compound.

Workup

  1. additionDowex 50WX2-200 ion exchanger resin is added and, within 1 h
  2. concentrationthe mixture is concentrated in a rotary evaporator
  3. washThe resin is washed successively with water, DMF, methanol, dichloromethane, methanol and 10% triethylamine in methanol
  4. concentrationThe product fraction is concentrated
  5. customchromatographed on silica gel (mobile phase: dichloromethane/methanol/triethylamine)
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-ab15d2c8410c4a2cadb478099f4a29bf
Source dataset
uspto-grants-2014_07
Patent number
US08772511B2

Linked notes

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