Diisopropylethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-dichloro-1-benzofuran-2-carboxamide hydrochloride

HRID 335581Notes

Reaction equation

HRID 335581 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl:14])[C:5]2[O:9][C:8]([C:10]([OH:12])=O)=[CH:7][C:6]=2[CH:13]=1.CN(C(ON1N=[N:30][C:25]2[CH:26]=[CH:27][CH:28]=[N:29][C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:39](N(CC)C(C)C)(C)[CH3:40]>CN(C=O)C>[ClH:1].[N:29]12[CH2:28][CH2:27][CH:26]([CH2:39][CH2:40]1)[C@@H:25]([NH:30][C:10]([C:8]1[O:9][C:5]3[C:4]([Cl:14])=[CH:3][C:2]([Cl:1])=[CH:13][C:6]=3[CH:7]=1)=[O:12])[CH2:24]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 47718415,7-dichlorobenzofuran-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 68431922N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5,7-dichloro-1-benzofuran-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

227 mg (0.98 mmol) of 5,7-dichlorobenzofuran-2-carboxylic acid, 200 mg (0.98 mmol) of R-3-aminoquinuclidine dihydrochloride, 449 mg (1.18 mmol) of HATU, 458 mg (3.54 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. An excess of 1N hydrochloric acid is then added to the product. The solvent is removed under reduced pressure. 169 mg (46% of theory) of the title compound are isolated.

Workup

  1. customThe reaction mixture is purified by preparative HPLC
  2. additionAn excess of 1N hydrochloric acid is then added to the product
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d55d88c6de254b0da3378d0e784d3e22
Source dataset
uspto-grants-2014_11
Patent number
US08884017B2

Reaction notes

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