HCID 68431800, compound → 5-Amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-methyl-1-benzothiophene-2-carboxamide dihydrochloride

HRID 658207Notes

Reaction equation

HRID 658207 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][C:16]=3[C:17]=1[CH3:18])=[O:12])[CH2:3]2>C(O)(=O)C.[Zn]>[ClH:1].[ClH:1].[NH2:23][C:20]1[CH:21]=[CH:22][C:15]2[S:14][C:13]([C:11]([NH:10][C@@H:4]3[CH:5]4[CH2:6][CH2:7][N:2]([CH2:9][CH2:8]4)[CH2:3]3)=[O:12])=[C:17]([CH3:18])[C:16]=2[CH:19]=1

Participants

4

Reactant 1

HCID 68431800HCID 68431800, compound

Product 1

HCID 684310805-Amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-methyl-1-benzothiophene-2-carboxamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

317 mg (0.83 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-methyl-5-nitro-1-benzothiophene-2-carboxamide hydrochloride are suspended in 2 ml of acetic acid. 300.0 mg (4.59 mmol) of zinc are added, and the mixture is then stirred at RT for 1 h. The reaction mixture is filtered through kieselguhr, and the filter cake is washed with methanol. The filtrate is concentrated under reduced pressure and the residue is purified by preparative HPLC. The product fraction is dissolved in 4M HCl in dioxane, concentrated under reduced pressure and recrystallized from acetonitrile. 154 mg (47.8% of theory) of the title compound are obtained.

Workup

  1. filtrationThe reaction mixture is filtered through kieselguhr
  2. washthe filter cake is washed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by preparative HPLC
  5. dissolutionThe product fraction is dissolved in 4M HCl in dioxane
  6. concentrationconcentrated under reduced pressure
  7. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-43e1cbfe75e94c81ae77060d2251ec35
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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