Sodium Iodide → Ethyl 2-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)thiazole-4-carboxylate

HRID 408848Notes

Reaction equation

HRID 408848 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:14]([O:16][C:17]([C:19]1[N:20]=[C:21]([CH2:24]Cl)[S:22][CH:23]=1)=[O:18])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[C:10]([O:9][C:7]([N:1]1[CH2:6][CH2:5][N:4]([CH2:24][C:21]2[S:22][CH:23]=[C:19]([C:17]([O:16][CH2:14][CH3:15])=[O:18])[N:20]=2)[CH2:3][CH2:2]1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 24715135Ethyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 58055816Ethyl 2-((4-(tert-butoxycarbonyl)piperazin-1-yl)methyl)thiazole-4-carboxylateYield 126.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 1-piperazinecarboxylate (1.811 g, 9.72 mmol), 2-chloromethyl-thiazole-4-carboxylic acid ethyl ester (2 g, 9.72 mmol), potassium carbonate (2.69 g, 19.45 mmol) and sodium iodide (0.292 g, 1.945 mmol) were combined and stirred in acetonitrile at reflux for 2 hours. The reaction was concentrated under reduced pressure. The residue was taken up in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to give the title compound (4.38 g).

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3b4687a8384452c8b90d6cc753e3cb8
Source dataset
uspto-grants-2014_06
Patent number
US08759352B2

Reaction notes

Loading…