Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-1-benzothiophene-2-carboxamide hydrochloride

HRID 335599

Reaction equation

HRID 335599 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([OH:13])=O.CN(C(ON1N=[N:29][C:24]2[CH:25]=[CH:26][CH:27]=[N:28][C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:38](N(CC)C(C)C)(C)[CH3:39]>CN(C=O)C>[ClH:1].[N:28]12[CH2:27][CH2:26][CH:25]([CH2:38][CH2:39]1)[C@@H:24]([NH:29][C:11]([C:3]1[S:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=1[Cl:1])=[O:13])[CH2:23]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3079643-Chloro-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 68431207N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-3-chloro-1-benzothiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

356.7 mg (1.68 mmol) of 3-chloro-1-benzothiophene-2-carboxylic acid, 334 mg (1.68 mmol) of R-3-aminoquinuclidine dihydrochloride, 765.3 mg (2.01 mmol) of HATU, 780.5 mg (6.04 mmol) of N,N-diisopropylethylamine and 2.0 ml of DMF are reacted according to the general procedure (variant B). The reaction mixture is purified by preparative HPLC. The product is dissolved in 4M HCl in dioxane and then reconcentrated. 265 mg (44.2% of theory) of the title compound are obtained. The analytical data correspond to those of the racemate (example 14).

Workup

  1. customThe reaction mixture is purified by preparative HPLC
  2. dissolutionThe product is dissolved in 4M HCl in dioxane

Sources & evidence

ORD record
ord-b745abf4289b439c8f2b28f8a9e66e9d
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Linked notes

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