2-(Chloroacetyl)thiophene → HCID 86660301, compound

HRID 453689Notes

Reaction equation

HRID 453689 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:20][C:21]2[CH:26]=[C:25]([F:27])[C:24]([F:28])=[C:23]([F:29])[CH:22]=2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N:14]([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:30][CH2:31][C:32]([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)=[O:33]>C(#N)C>[Cl-:30].[F:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:20][C:21]2[CH:22]=[C:23]([F:29])[C:24]([F:28])=[C:25]([F:27])[CH:26]=2)[C:9]([O:11][C@@H:12]2[CH:17]3[CH2:18][CH2:19][N+:14]([CH2:31][C:32](=[O:33])[C:34]4[S:35][CH:36]=[CH:37][CH:38]=4)([CH2:15][CH2:16]3)[CH2:13]2)=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 58556901HCID 58556901, compound

Product 1

HCID 86660301HCID 86660301, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(R)-Quinuclidin-3-yl 2-(3-fluorophenyl)-2-(3,4,5-trifluorophenylamino)acetate (I43) (85 mg, 0.21 mmol) and 2-chloro-1-(thiophen-2-yl)ethanone (35.1 mg, 0.22 mmol) were dissolved in acetonitrile (5 ml) and stirred at room temperature for 48 hours. The solvent was evaporated, and the resulting crude compound was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-3-(2-(3-fluorophenyl)-2-(3,4,5-trifluorophenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (70 mg; 59% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe resulting crude compound was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-b0d04bd1a1ca4013ae346a0689e62d59
Source dataset
uspto-grants-2013_07
Patent number
US08492548B2

Reaction notes

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