Methanesulfonyl chloride, DMSO

Scheme 25. Reagents and conditions (a) R sAI, Cul-2 LiCI, THF, 0°C (b) PivCI, py (c) 4-dimethylaminopyridine (DMAP) (3 equiv.), NaNa (20 equiv.), methanesulfonyl chloride (MsCI) (3 equiv.), RT then DMSO 3 h (d) UAIH4 (e) B0C2O, EtgN, CH2CI2.

DMAP (40 xL, 8.0 tmol, 0.1 eq, 0.2 M in anhydrous DCE), and methanesulfonyl chloride (320 xL, 160 xmol, 2.0 eq, 0.5 M in anhydrous DCM) were added to a 10x95 mm test tube. The test tube was sealed with a test tube cap and stirred in glove box for 3 h at ambient temperature. The solvent was evaporated (SpeedVac or GeneVac, vacuum, medium heat, 16 h) and the residue was dissolved in anhydrous DMF (400 p,L). TEA (80 xL, 80.0 xmol, 1.0 eq, 1 M in anhydrous DMF) and the amine (480 xL, 240.0 xmol, 3.0 eq, 0.5 M in anhydrous DMF) were added. The test tube was sealed with a test tube cap. The reaction was heated and stirred at 80°C for 5 h. The solvent was evaporated (SpeedVac or GeneVac, vacuum, medium heat, 16 h), and the residue was dissolved in DMSO (1.340 mL). The reaction mixtures were analyzed by LCMS and the products isolated by automated mass-directed HPLC. 

Scheme 17 Synthesis of polyamine-imidazole conjugates. Reagents and conditions a aminoalcohol, CFI2CI2, 2h, rt b methanesulfonyl chloride, pyridine, 30 min, rt c 211, DMSO, 32h, 70 °C d 212, DMSO, 5h, 50 °C e 1 1 TFA CH2Cl2, 1 h, rt / NaOH then CH2CI2, chromatography g 20% Pd(OH)2/C, H2, MeOH, 4h ii H2O, HCl/EtOH, 3h, 0 °C then rt [246]...

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