2-(Chloroacetyl)thiophene → HCID 70673626, compound

HRID 1910497Notes

Reaction equation

HRID 1910497 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10](=[S:27])[O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:2]2.[Cl:28][CH2:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31]>C(OCC)(=O)C>[Cl-:28].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:10]([NH:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][C:30](=[O:31])[C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[S:27])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 86762176HCID 86762176, compound

Product 1

HCID 70673626HCID 70673626, compoundYield 24.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—O-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamothioate (60 mg, 0.15 mmol) in ethyl acetate (1 ml), 2-chloro-1-(thiophen-2-yl)ethanone (27.3 mg, 0.17 mmol) was added. The reaction was stirred at room temperature for 3 days. The solvent was evaporated, and the residue was purified by flash chromatography (DCM/MeOH=75/25) to obtain (R)-3-((bis(3-fluorophenyl)methoxy)carbonothioylamino)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (20 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=75/25)

Sources & evidence

ORD record
ord-a090c3a0857f4902be2ee7deb750e512
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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