2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → 4-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromide

HRID 1910518Notes

Reaction equation

HRID 1910518 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[Br:26][CH2:27][C:28]([C:30]1[S:31][CH:32]=[CH:33][N:34]=1)=[O:29]>CCOC(C)=O>[Br-:26].[F:25][C:21]1[CH:20]=[C:19]([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[O:10][C:8]([CH:5]2[CH2:4][CH2:3][N+:2]([CH3:1])([CH2:27][C:28](=[O:29])[C:30]3[S:31][CH:32]=[CH:33][N:34]=3)[CH2:7][CH2:6]2)=[O:9])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 70925814Bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate

Product 1

HCID 866729524-((Bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromideYield 70.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of bis(3-fluorophenyl)methyl 1-methylpiperidine-4-carboxylate (106 mg, 0.31 mmol, prepared as in example 40) in EtOAc (3 ml), 2-bromo-1-(thiazol-2-yl)ethanone (63.2 mg, 0.31 mmol) was added. The mixture was stirred at room temperature for 27 hours. The solvent was evaporated, and the crude was triturated with Et2O and collected by filtration. The compound was purified by flash chromatography (DCM/MeOH=95/5 to 9/1) to obtain 4-((bis(3-fluorophenyl)methoxy)carbonyl)-1-methyl-1-(2-oxo-2-(thiazol-2-yl)ethyl)piperidinium bromide (120 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O
  3. filtrationcollected by filtration
  4. customThe compound was purified by flash chromatography (DCM/MeOH=95/5 to 9/1)

Sources & evidence

ORD record
ord-7cc09076f07d416795c1f1b750386435
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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