2-Chloroacetophenone → HCID 86660340, compound

HRID 469513Notes

Reaction equation

HRID 469513 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:41]=[CH:40][CH:39]=[CH:38][C:33]=2[C:34]([O:36][CH3:37])=[O:35])[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.CC#N.O.C(Cl)Cl.CO>CCOC(C)=O>[Cl-:1].[CH3:37][O:36][C:34]([C:33]1[CH:38]=[CH:39][CH:40]=[CH:41][C:32]=1[NH:31][CH:19]([C:16]1[CH:17]=[N:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=1)[C:20]([O:21][C@@H:22]1[CH:27]2[CH2:26][CH2:25][N+:24]([CH2:2][C:3](=[O:4])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)([CH2:29][CH2:28]2)[CH2:23]1)=[O:30])=[O:35]

Participants

6

Reactant 4

HCID 107572-ChloroacetophenoneHCID 18373917Acetonitrile--water (1/1)HCID 21226129Dichloromethane methanolHCID 58557033HCID 58557033, compound

Product 1

HCID 86660340HCID 86660340, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (57.7 mg, 0.37 mmol) was added to a solution of methyl 2-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C80) (159 mg, 0.37 mmol) in EtOAc (3 ml), and the resulting reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the crude was purified first by flash chromatography (DCM/MeOH=97/3 to 9/1), then by preparative HPLC (Eluent: CH3CN/H2O) and finally by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(2-(2-(methoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (21.2 mg, 9.8% yield).

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated
  3. customthe crude was purified first by flash chromatography (DCM/MeOH=97/3 to 9/1)

Sources & evidence

ORD record
ord-8f6664d82110426db86e1990161fc9b7
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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