2-(Chloroacetyl)thiophene → HCID 86672930, compound

HRID 1910494Notes

Reaction equation

HRID 1910494 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10](=[O:29])[O:11][CH:12]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH2:2]2.[Cl:30][CH2:31][C:32]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)=[O:33]>C(OCC)(=O)C.C(#N)C>[Cl-:30].[O:33]=[C:32]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)[CH2:31][N+:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([NH:9][C:10]([O:11][CH:12]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:22])[F:21])=[CH:17][CH:18]=1)=[O:29])[CH2:2]2

Participants

5

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 70938623HCID 70938623, compound

Product 1

HCID 86672930HCID 86672930, compoundYield 37.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Phenyl(4-(trifluoromethyl)phenyl)methyl(R)-quinuclidin-3-ylcarbamate (56.0 mg, 0.14 mmol) was dissolved in ethyl acetate (1 ml) and acetonitrile (0.5 ml). The resulting solution was treated with 2-chloro-1-(thiophen-2-yl)ethanone (24.0 mg, 0.15 mmol) and stirred at room temperature overnight. The solvent was evaporated, and the crude was first purified by flash chromatography (DCM/MeOH=95/5) and then by preparative HPLC(CH3CN/H2O) to afford (3R)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-3-((phenyl(4-(trifluoromethyl)phenyl)methoxy)carbonylamino)-1-azoniabicyclo[2.2.2]-octane chloride (30.0 mg, mixture of diastereoisomers).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was first purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-eaf802e706184de695162e227629255d
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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