[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[NH2:13])=[CH:3][CH:2]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16].N.CO.CCOC(C)=O>ClCCCl.CCCCCC>[CH3:14][S:15]([NH:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)(=[O:17])=[O:16]
A solution of 2-(4-pyridyl)phenylamine (Step b) (500 mg, 2.9 mmol) in 1,2-dichloroethane (35 mL) was stirred magnetically under N2 in a 100 mL round-bottomed flask at 25° C. The solution was treated with TEA (Aldrich) (400 μL, 2.9 mmol) followed by methanesulfonyl chloride (Aldrich) (230 μL, 335 mg, 2.9 mmol). The vessel was heated in a 50° C. oil bath for 3 h. The reaction mixture was concentrated in vacuo and the resulting residue was partitioned between EtOAc (100 mL) and satd NaHCO3 (50 mL). The organic layer was washed with satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford a yellow oil. To the oil was added 5:25:75 1 M NH3/MeOH:EtOAc:hexane (10 mL). A yellow precipitate formed which was collected by filtration and dried in vacuo at 40° C. to afford the title compound as a yellow solid (480 mg). MS (ESI, pos. ion) m/z: 249 (M+1); (ESI, neg. ion) m/z: 247 (M−1). Calc'd for C12H12N2O2S: 248.30.
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