1-(2-Hydroxyethyl)piperazine → 2-[4-(2-Hydroxyethyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

HRID 1392958Notes

Reaction equation

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

Participants

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-(2-hydroxyethyl)piperazine 14c (156 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 15c (185 mg, 68.2%).

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-dcd0bd5e93104dd9bf548dcb30c964eb
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345043B2

Reaction notes

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