2-Chloroacetophenone → HCID 86660339, compound

HRID 469510Notes

Reaction equation

HRID 469510 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F:11][C:12]1[CH:13]=[C:14]([NH:18][CH:19]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:21])[CH:15]=[CH:16][CH:17]=1.CC#N.O>CCOC(C)=O>[Cl-:1].[F:11][C:12]1[CH:13]=[C:14]([NH:18][CH:19]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[C:20]([O:22][C@@H:23]2[CH:28]3[CH2:27][CH2:26][N+:25]([CH2:2][C:3](=[O:4])[C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)([CH2:30][CH2:29]3)[CH2:24]2)=[O:21])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 107572-ChloroacetophenoneHCID 18373917Acetonitrile--water (1/1)HCID 58557009HCID 58557009, compound

Product 1

HCID 86660339HCID 86660339, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-1-phenylethanone (26.9 mg, 0.17 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(3-fluorophenylamino)-2-(6-methoxypyridin-3-yl)acetate (C77) (67.1 mg, 0.17 mmol) in EtOAc (3 mL), and the resulting reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the crude product was purified by flash chromatography (DCM/MeOH=97/3 to 9/1) and then by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-fluorophenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (19.5 mg, 20.7% yield).

Workup

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

Sources & evidence

ORD record
ord-68392330f14e414fb94c3d4fd9e656e6
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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