2-Chloro-N-pyridin-2-yl-acetamide → (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469462

Reaction equation

HRID 469462 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:4].[S:12]1[CH:16]=[C:15]([CH:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[C:14]2[CH:36]=[CH:37][CH:38]=[CH:39][C:13]1=2>CCOC(C)=O>[Cl-:1].[S:12]1[CH:16]=[C:15]([CH:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23]([CH2:2][C:3](=[O:4])[NH:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[C:14]2[CH:36]=[CH:37][CH:38]=[CH:39][C:13]1=2

Participants

4

Reactant 2

HCID 2894352-Chloro-N-pyridin-2-yl-acetamideHCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

Product 1

HCID 54765168(R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chlorideYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-N-(pyridin-2-yl)acetamide (43.5 mg, 0.25 mmol) was added portion-wise to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (C19) (100 mg, 0.25 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was purified by preparative HPLC (Eluent: CH3CN, H2O). The product was triturated with i-Pr2O, filtered and dried under vacuum at room temperature to obtain (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (31 mg, 21.6% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (Eluent: CH3CN, H2O)
  3. customThe product was triturated with i-Pr2O
  4. filtrationfiltered
  5. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-6ce602d1f2004402a1bb3b9b2b7a1f3d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Linked notes

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