2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469464Notes

Reaction equation

HRID 469464 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)=[O:4].[S:10]1[CH:14]=[C:13]([CH:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2>CCOC(C)=O>[Br-:1].[S:10]1[CH:14]=[C:13]([CH:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N+:21]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][N:9]=4)([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2

Participants

4

Reactant 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

Product 1

HCID 54765170(R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 28.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiazol-2-yl)ethanone (52.5 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 precipitate was filtered, washed with EtOAc and purified by preparative HPLC (Eluent: CH3CN, H2O) to obtain (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (42 mg, 27.5% yield).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with EtOAc
  3. custompurified by preparative HPLC (Eluent: CH3CN, H2O)

Sources & evidence

ORD record
ord-4350582e316541b986fc4ad34d2c8bfa
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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