3-PHENYLBENZENESULFONYL CHLORIDE

The title compound was prepared according to General Procedure J from [1 , 1'-biphenyi]-3- yl(benzyl)s.ulfane (450 mg, 1.63 mmoS). The crude product was purified by Gombiflash silica gel chromatography ( 00percent hexane), which provided 250 mg (5.9percent) of the title compound as aA. A. glass vial with a septum cap was fitted with a magnetic stirbar, charged with novenamine hydrochloride (30 mg, 0.06 mmol, 1.3 eq.), and sparged with positive N2 pressure and a vent needle for 10 minutes. Pyridine (1 mL) was added and the mixture was cooled to -40 C with stirring. A solution of [l, r-biphenyl]-3-sulfonyl chloride (13.0 mg, 0.05 mmol, 1.0 eq.) in 0.5 mL of pyridine was added and the mixture was stirred under a N2 atmosphere for 12 h, letting the bath warm up to 23 C. The solvent was subsequently removed by rotary evaporation and the material was subjected to normal phase silica gel column chromatography (DCM/MeOH) monitoring at 340 nm. Fractions containing the product were concentrated, hi-vaced, and further purified by reverse-phase HPLC with a Zorbax C18 column with acetonitrile/water as the eluent (80% MeCN to 100% MeCN over the course of 20 minutes). Fractions containing the product were concentrated by rotary evaporation and hi-vaced to yield the title compound as a white solid (10 mg, 32%).EXAMPLE 139 N-(4-chloro-3-methyl-5-isoxazolyl)-3-biphenylsulfonamide N-(4-chloro-3-methyl-5-isoxazolyl)-3-1-phenylsulfonamide was prepared in the same manner as described in from 5-amino-4-chloro-3-methylisoxazole and 3-biphenylsulfonyl chloride in 63% yield. This was purified by HPLC (5% CH3 CN to 100% CH3 CN over 30 min.) to give a solid, m.p. 84-86 C.

Molecular Weight:252.72
XLogP3:4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:252.0011784
Monoisotopic Mass:252.0011784
Topological Polar Surface Area:42.5
Heavy Atom Count:16
Complexity:314
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes