ChemicalBook CAS DataBase List PYRIDINE-2-SULFONYL CHLORIDE

PYRIDINE-2-SULFONYL CHLORIDE synthesis

7synthesis methods

Product Name:PYRIDINE-2-SULFONYL CHLORIDE
CAS Number:66715-65-9
Molecular formula:C5H4ClNO2S
Molecular Weight:177.61

24367-66-6
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66715-65-9
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$117.00/50mg

Yield:-

Reaction Conditions:

with N-chloro-succinimide in dichloromethane

Steps:

278
Example 278; N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2-pyridinesulfonamide; To a suspension of sodium 2-pyridinesulfinate (48.4 mg, 0.291 mmol) in dichloromethane (3 ml) was added N-chlorosuccinimide (38.9 mg, 0.291 mmol). After 1 hour, the reaction mixture was filtered through a short Celite plug. To the crude sulfonyl chloride solution was added the 4-[4-(3-amino-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinamine (50 mg, 0.146 mmol) and pyridine (0.035 ml, 0.437 mmol), and the mixture was stirred for 3 hours at ambient temperature. After 3 hours, the reaction was quenched with methanol, and the crude reaction mixture was concentrated, redissolved in methanol, and purified via reversed-phase HPLC chromatography, eluting with 30-60% acetonitrile/0.1% aqueous trifluoroacetic acid. The desired fractions were combined, neutralized with aqueous saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the title compound (8.8 mg, 12%) as tan solid. MS (ESI): 485 [M+H]⁺.

References:

Adams, Jerry Leroy;Dickerson, Scott Howard;Johnson, Neil W.;Kuntz, Kevin;Petrov, Kimberly;Ralph, Jeffrey M.;Rheault, Tara Renae;Schaaf, Gregory;Stellwagen, John;Tian, Xinrong;Uehling, David Edward;Waterson, Alex Gregory;Wilson, Brian US2009/298815, 2009, A1 Location in patent:Page/Page column 183

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2637-34-5 Synthesis