[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:38][C:39]1[CH:40]=[C:41]([S:45]([NH2:48])(=[O:47])=[O:46])[CH:42]=[CH:43][CH:44]=1.C(N(CC)CC)C>CN(C=O)C>[C:1]([C:5]1[N:10]=[CH:9][C:8]([C:11]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([S:45]([NH2:48])(=[O:46])=[O:47])[CH:40]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]
A solution of 6-tert-butylpyridine-3-carboxylic acid (18 mg, 0.10 mmol) and HATU (38 mg, 0.10 mmol) in DMF (1 mL) was stirred at room temperature for 3 minutes. To this solution was added 3-amino-benzenesulfonamide (17 mg, 0. 10 mmol) and triethylamine (28 μL, 0.20 mmol). The reaction was stirred at room temperature for 16 h and purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 6-tert-butyl-N-(3-(aminosulfonyl)phenyl)pyridine-3-carboxamide. LC/MS: m/z 334.3 (M+H)+ at 1.99 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
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