2-Chloroacetophenone → HCID 86660316, compound

HRID 453705Notes

Reaction equation

HRID 453705 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[O:11]=[C:12]([O:30][C@@H:31]1[CH:36]2[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]2)[CH2:32]1)[CH:13]([NH:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([OH:26])=[O:25])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(#N)C.CN(C=O)C>[Cl-:1].[C:24]([C:23]1[CH:22]=[C:21]([NH:20][CH:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:12]([O:30][C@@H:31]2[CH:36]3[CH2:37][CH2:38][N+:33]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:34][CH2:35]3)[CH2:32]2)=[O:11])[CH:29]=[CH:28][CH:27]=1)([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556907HCID 58556907, compound

Product 1

HCID 86660316HCID 86660316, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-1-phenylethanone (I19) (24.4 mg, 0.16 mmol) was added to a solution of 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoic acid (I5) (60 mg, 0.16 mmol) in acetonitrile (1 ml) and DMF (1 ml). The reaction mixture was stirred at room temperature for 24 hours. The solvent was evaporated, and the residue was purified by preparative HPLC (eluents CH3CN/H2O) to obtain (3R)-3-(2-(3-carboxyphenylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (12 mg, 14.2% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (eluents CH3CN/H2O)

Sources & evidence

ORD record
ord-3b178658110447cb9b9f7f7985a5541b
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

Loading…