Methyl iodide → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide

HRID 469503Notes

Reaction equation

HRID 469503 reaction equation
[I:1][CH3:2].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]([NH:23][C:24]2[CH:25]=[C:26]([CH:32]=[CH:33][CH:34]=2)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:12](=[O:22])[O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]3)[CH2:15]2)=[CH:7][CH:6]=1>CCOC(C)=O>[I-:1].[CH2:30]([O:29][C:27]([C:26]1[CH:25]=[C:24]([NH:23][CH:11]([C:8]2[CH:9]=[N:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[C:12]([O:13][C@@H:14]2[CH:19]3[CH2:20][CH2:21][N+:16]([CH3:2])([CH2:17][CH2:18]3)[CH2:15]2)=[O:22])[CH:34]=[CH:33][CH:32]=1)=[O:28])[CH3:31]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

Product 1

HCID 67124884(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodideYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Iodomethane (7.1 μl, 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. The solvent was evaporated, and the residue was triturated with Et2O, filtered and dried. The product was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-methyl-1-azoniabicyclo[2.2.2]octane iodide (24.3 mg, 36.7% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried
  5. customThe product was purified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-411c0350a18547b3a153d38184e4c314
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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