2-Chloroacetophenone → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469498Notes

Reaction equation

HRID 469498 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][O:12][C:13]1[N:18]=[CH:17][C:16]([CH:19]([NH:31][C:32]2[CH:33]=[C:34]([CH:40]=[CH:41][CH:42]=2)[C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:20](=[O:30])[O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[CH:15][CH:14]=1>CCOC(C)=O>[Cl-:1].[CH2:38]([O:37][C:35]([C:34]1[CH:33]=[C:32]([NH:31][CH:19]([C:16]2[CH:17]=[N:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[C:20]([O:21][C@@H:22]2[CH:27]3[CH2:28][CH2:29][N+:24]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:25][CH2:26]3)[CH2:23]2)=[O:30])[CH:42]=[CH:41][CH:40]=1)=[O:36])[CH3:39]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Product 1

HCID 86660333(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 40.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (17.6 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight, and then the solvent was evaporated to dryness. The residue was triturated with Et2O and then purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (26.3 mg, 38.9% yield).

Workup

  1. customthe solvent was evaporated to dryness
  2. customThe residue was triturated with Et2O
  3. custompurified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-15a58531373040699ba4e6d443a6554b
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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