Hydrochloric Acid → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochloride

HRID 15467

Reaction equation

HRID 15467 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([C:12]([OH:14])=O)=[CH:9][C:8]=2[CH:15]=1)([O-:3])=[O:2].CN(C(ON1N=[N:31][C:26]2[CH:27]=[CH:28][CH:29]=[N:30][C:25]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:40](N(CC)C(C)C)(C)[CH3:41].CN(C=O)C.[ClH:54]>C(OCC)C>[ClH:54].[N:30]12[CH2:29][CH2:28][CH:27]([CH2:40][CH2:41]1)[C@@H:26]([NH:31][C:12]([C:10]1[S:11][C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][C:8]=3[CH:9]=1)=[O:14])[CH2:25]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2389395-Nitro-1-benzothiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 68429753N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

420 mg (1.88 mmol) of 5-nitro-1-benzothiophene-2-carboxylic acid, 374.7 mg (1.88 mmol) of R-3-aminoquinuclidine dihydrochloride, 858.6 mg (2.26 mmol) of HATU, 875.5 mg (6.78 mmol) of N,N-diisopropylethylamine and 2.0 ml of DMF are reacted according to the general procedure (variant B). The resulting precipitate is suspended in 1N HCl in diethyl ether, filtered off, washed twice with dichloromethane and dried under high vacuum. 523 mg (75.6% of theory) of the title compound are obtained.

Workup

  1. filtrationfiltered off
  2. washwashed twice with dichloromethane
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-69e662f944e041839663520ec6fed934
Source dataset
uspto-grants-2010_06
Patent number
US07732477B2

Linked notes

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