Acetonitrile → HCID 69201758, compound

HRID 1392962Notes

Reaction equation

HRID 1392962 reaction equation
Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[C:11]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2CC)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[C:31](#N)[CH3:32]>>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([N:20]2[CH2:19][CH2:18][N:17]([CH2:11][CH2:16][C:15]3[CH:14]=[CH:13][CH:12]=[CH:32][CH:31]=3)[CH2:22][CH2:21]2)=[N:6][CH:5]=1)=[O:8]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2773502Methyl 2-bromothiazole-5-carboxylateHCID 200993912-Ethyl-1-phenylpiperazine

Product 1

HCID 69201758HCID 69201758, compoundYield 66.4%

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-phenyl ethyl piperazine 14e (228 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 15e (245 mg, 66.4%).

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-5b177eb5073240f8abd5e7308d5775fd
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

Loading…