2-Bromo-1-(thiophen-3-yl)ethan-1-one → HCID 54764990, compound

HRID 469456Notes

Reaction equation

HRID 469456 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].[O:10]=[C:11]([O:29][C@@H:30]1[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1)[CH:12]([NH:19][C:20]1[CH:24]=[CH:23][S:22][C:21]=1[C:25]([O:27][CH3:28])=[O:26])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOC(C)=O>[Br-:1].[CH3:28][O:27][C:25]([C:21]1[S:22][CH:23]=[CH:24][C:20]=1[NH:19][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:11]([O:29][C@@H:30]1[CH:35]2[CH2:34][CH2:33][N+:32]([CH2:2][C:3](=[O:4])[C:5]3[CH:9]=[CH:8][S:7][CH:6]=3)([CH2:37][CH2:36]2)[CH2:31]1)=[O:10])=[O:26]

Participants

4

Reactant 2

HCID 27763792-Bromo-1-(thiophen-3-yl)ethan-1-oneHCID 46840422HCID 46840422, compound

Product 1

HCID 54764990HCID 54764990, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-1-(thiophen-3-yl)ethanone (25.6 mg, 0.12 mmol) was added to a solution of methyl 3-(2-oxo-1-phenyl-2-((R)-quinuclidin-3-yloxy)ethylamino)thiophene-2-carboxylate (C11) (50 mg, 0.12 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight, and then the solvent was evaporated under vacuum. The residue was triturated with Et2O and then purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (3R)-3-(2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetoxy)-1-(2-oxo-2-(thiophen-3-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (44.3 mg, 58.6% yield).

Workup

  1. customthe solvent was evaporated under vacuum
  2. customThe residue was triturated with Et2O
  3. custompurified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-a175476e8e2149b3a8a1c891f352d0c6
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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