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10-cyclopropyl-2-(cis-3,5-dimethylpiperazin-1-yl)-3-fluoro-7-hydroxy-6,7,7,8,10-tetrahydropyrido<2',3':4,5>imidazo<1,2-c>pyrimidine-6,8-dione[ No CAS ]
2,6-dichloro-5-fluoropyridine-3-sulfonylchloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With hydrogenchloride; thionyl chloride; copper(l) chloride; sodium nitrite; In water; at 0 - 20℃; for 1.41h;
a flask containing H2O (20 mL) was cooled to 0 C. Thionyl chloride (4.41 mL, 60.8 mmol) was then added dropwise very slowly maintaining the internal temperature below 7 C. Upon complete addition, the mixture is slowly warmed to rt and stirred at rt for 4 h. copper (i) chloride (55 mg, 0.55 mmol) was then added and solution was cooled to 0 C. meanwhile, a separate flask containing 2,6- dichloro-5-fluoropyridin-3-amine (2.0 g, 11.0 mmol) and concentrated Hcl (14 mL) was cooled to 0 C before addition of a solution of sodium nitrite (1.11 g, 16.0 mmol) in H2O (10 mL). The resulting diazonium solution was stirred at 0 C for 15 min then added dropwise to the flask containing the thionyl chloride and copper (i) chloride mixture over a period of 10 min. after addition, the mixture was stirred at 0 C for 1 h then diluted with cH<SUb>2</SUb>cl<SUb>2</SUb> (2 x 30 mL). The organic extracts were combined, dried (mgSO<SUb>4</SUb>), filtered and concentrated under reduced pressure to provide 2,6-dichloro-5-fluoropyridine-3-sulfonyl chloride (2.4 g, 82% yield) which was used directly in the next step without further purification.
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