Stannous Chloride → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

HRID 658191Notes

Reaction equation

HRID 658191 reaction equation
[Sn](Cl)Cl.[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2>CN(C=O)C.CO>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]1)[C@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 59341419N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide

Product 1

HCID 59341411N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

2.0 ml (4 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide (135 mg, 0.32 mmol), and the mixture is stirred at RT for 18 h. The crude product is taken up in methanol and shaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min. The loaded ion exchanger is washed three times with in each case 30 ml of methanol, then with water/methanol 8:2, again with methanol, with dichloromethane and finally again with methanol. The product is eluted using methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator, and 20 ml of 1N aqueous sodium hydroxide solution are added to the crude mixture. The aqueous phase is extracted six times with in each case 20 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and the solvent is removed under reduced pressure using a rotary evaporator. 100.7 mg (82% of theory) of the title compound are isolated. The analytical data correspond to those of the enantiomeric compound from example 32.

Workup

  1. stirringshaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min
  2. washThe loaded ion exchanger is washed three times with in each case 30 ml of methanol
  3. washThe product is eluted
  4. customThe solvent is removed under reduced pressure
  5. customa rotary evaporator, and 20 ml of 1N aqueous sodium hydroxide solution
  6. additionare added to the crude mixture
  7. extractionThe aqueous phase is extracted six times with in each case 20 ml of ethyl acetate
  8. dry with materialThe combined organic phases are dried over magnesium sulfate
  9. customthe solvent is removed under reduced pressure
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-c16725a0445340ba9cd9d3bbf4b8f184
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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