Potassium Carbonate → HCID 69197930, compound

HRID 1392957Notes

Reaction equation

HRID 1392957 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([N:21]2[CH2:22][CH2:23][N:18]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:19][CH2:20]2)=[N:6][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 759941-BenzylpiperazineHCID 2773502Methyl 2-bromothiazole-5-carboxylate

Product 1

HCID 69197930HCID 69197930, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-bromothiazole-5-carboxylate 1 (222 mg, 1.00 mmol) in acetonitrile (20 mL) were added N-benzyl piperazine 14b (211 mg, 1.20 mmol) and potassium carbonate (152 mg, 1.10 mmol) under a N2 atmosphere. The reaction mixture was heated to reflux at 80° C. for 10 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography using silica gel to give the compound 15b (229 mg, 72.7%).

Workup

  1. temperatureThe reaction mixture was heated
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-454ac3d541854d41a7fcd1532088f8f2
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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