Piperazine → Methyl 2-(piperazin-1-yl)thiazole-5-carboxylate

HRID 1392937Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][O:9][C:7]([C:4]1[S:3][C:2]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:6][CH:5]=1)=[O:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 2-bromothiazole-5-carboxylate (1a) (5.00 g, 22.50 mmol) in acetonitrile (50 mL) were added piperazine 2 (2.32 g, 26.97 mmol) and potassium carbonate (6.22 g, 45.05 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 11 as a solid (4.10 g, 79.8%). HPLC: 92% (Rt=3.883 min).

Workup

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

Sources & evidence

ORD record: ord-cb7415fab9f94c848dd0a346512519be
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345043B2

Reaction notes

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