[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[C:18]([CH3:19])=[CH:17][O:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].S(OC)(O[CH3:26])(=O)=O.Cl>CO.C(Cl)(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH3:26])[C:10]2[C:11]3[C:18]([CH3:19])=[CH:17][O:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:7][CH:8]=1To a 25 mL round bottom flask was weighed 7 (51 mg, 0.2 mmol) and was added DMF (2 mL) to afford a solution. The flask was purged with argon for five min followed by cooling down to 0° C. using ice bath. Sodium hydride (14.4 mg, 0.6 mmol) was added to the solution at 0° C. The solution was stirred for 30 min at 0° C. under argon atmosphere. Dimethyl sulfate (75.7 mg; ≈57 μl; 0.6 mmol) was injected to the reaction mixture and the flask was warmed to room temperature. The mixture was stirred at room temperature for another 3 h at the end of which 1 N Hydrochloric acid (5 mL) was added carefully to quench the reaction followed by water (20 mL) to afford a precipitate. Product was extracted using ethyl acetate (10 mL×2). Combined organic extracts were washed with brine (10 mL) dried (anhydrous sodium sulfate) and concentrated under reduced pressure. Silica gel (200 mg) was added and solvent evaporated to afford a plug. Column chromatography by elution with hexanes:ethyl acetate (5:1) afforded AAG16 (20 mg; 37%) as light brown semisolid; which was triturated withl hexanes to afford light brown solid. TLC Rf0.79 (CHCl3:MeOH, 10:1); mp 84-85.6° C.; 1HNMR (400 MHz) (DMSO-d6): δ 1.036-1.039 (d, 3H, CH3, J=1.2 Hz); 3.423 (s, 3H, NCH3), 3.752 (s, 3H, OCH3), 6.944-6.967 (d, 2H, C6H4, J=9.2 Hz), 7.176-7.199 (d, 2H, C6H4, J=9.2 Hz), 7.505-7.508 (d, 1H, C6-CH, J=1.2 Hz), 8.234 (s, 1H, C2-CH). Anal. Calcd for C15H15N3O2.0.28 C6H14.0.05 HCl: C, 67.84; H, 6.48; N, 14.22; Found: C, 67.89; H, 6.18; N, 14.06.
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