N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-nitro-1-benzothiophene-2-carboxamide hydrochloride → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-amino-1-benzothiophene-2-carboxamide dihydrochloride

HRID 658214Notes

Reaction equation

HRID 658214 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]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:16]=3[C:17]=1[Cl:18])=[O:12])[CH2:3]2>[Sn](Cl)Cl.CN(C=O)C>[ClH:18].[ClH:1].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:22]=[C:21]([NH2:23])[CH:20]=[CH:19][C:16]=3[C:17]=1[Cl:18])=[O:12])[CH2:3]2

Participants

4

Reactant 1

HCID 68431015N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-nitro-1-benzothiophene-2-carboxamide hydrochloride

Product 1

HCID 68431670N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-amino-1-benzothiophene-2-carboxamide dihydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24479Stannous ChlorideSolvent

Procedure

83 mg (0.23 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-chloro-6-nitro-1-benzothiophene-2-carboxamide hydrochloride are dissolved in 1.5 ml of 2M tin(II) chloride solution in DMF and stirred at RT for 14 h. The reaction mixture is purified by preparative HPLC. The product fractions are concentrated, dissolved in a mixture of methanol and 4M HCl in dioxane, then again concentrated and dried under high vacuum. 53 mg (57.2% of theory) of the title compound are obtained.

Workup

  1. customThe reaction mixture is purified by preparative HPLC
  2. concentrationThe product fractions are concentrated
  3. dissolutiondissolved in a mixture of methanol and 4M HCl in dioxane
  4. concentrationagain concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e163a87a732b4bacaf4585f8bab62a6e
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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