Piperazine → HCID 68679497, compound

To a mixture of 330 mg (1.00 mmol) of (6-(5-bromo-3-methoxymethyl-3H-thiazol-2-ylideneamino)-pyridin-2-yl)-methanol, 0.348 ml (2.00 mmol) of N,N-diisopropylethylamine and 15 ml of chloroform was added 0.116 ml (1.50 mmol) of methanesulfonyl chloride at room temperature followed by stirring for 1 hour. The reaction mixture was washed with brine, the organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The resulting residue was dissolved in 4 ml of dimethyl sulfoxide and dropped into 2 ml of a solution of 861 mg (10.0 mmol) of piperazine in dimethyl sulfoxide and the mixture was stirred at room temperature for 4 hours and 30 minutes. The reaction solution was filtered and purified by a reversed phase preparative liquid chromatography to give 281 mg (0.706 mmol) of the title compound as a white solid.

1. washThe reaction mixture was washed with brine
2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
3. filtrationfiltered
4. concentrationthe filtrate was concentrated in vacuo
5. dissolutionThe resulting residue was dissolved in 4 ml of dimethyl sulfoxide
6. stirringthe mixture was stirred at room temperature for 4 hours and 30 minutes
7. filtrationThe reaction solution was filtered
8. custompurified by a reversed phase preparative liquid chromatography

ORD record

ord-5ead48011a664bbca56ae4af4ec02366

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491720B2