A. V. Joshua et al. / Bioorg. Med. Chem. Lett. 17 (2007) 4066–4069
4069
15. Compound 10 (298 mg, 0.51 mmol) was suspended in
dry ethanol (5 mL) at 0 ꢁC and to it, potassium iodide
(93 mg, 0.56 mmol), hydrochloric acid (1 N, 4 mL), and
hydrogen peroxide (30%, 1 mL) were added portionwise
with constant stirring. The reaction mixture was brought
to room temperature and stirred for another 2 h. The
excess of H2O2 was removed by adding dropwise
saturated solution of sodium disulfite (7 mL) with
stirring. The resulting reaction mixture was neutralized
cautiously with solid sodium bicarbonate and extracted
with dichloromethane. The organic layer was separated
and dried over Na2SO4. After evaporation of the solvent
in vacuum, the residue was taken up in benzene (20 mL)
and washed with cold hydrochloric acid (0.25 N, 25 mL).
The aqueous layer was separated and made alkaline with
concentrated ammonium hydroxide, extracted with
dichloromethane (3 · 10 mL). The organic layer was
separated, dried over Na2SO4, and evaporation of the
solvent in vacuum gave a yellow colored solid, which
was crystallized from benzene–hexane to give 172 mg
(yield 81%) of the final product 2, mp 181–182 ꢁC. 1H
NMR (500 MHz, CDCl3) d in ppm: 2.48 (s, 3H, CH3),
2.57 (br s, 4H, 2 · ÀCH2–, J = 5.0 Hz), 3.50 (br s, 4H,
2 · ÀCH2–, J = 5.0 Hz), 4.95 (s, 1H, NH), 6.45 (d, 1H,
Ar-H), 6.85 (d, 1H, Ar-H), 7.15 (t, 1H, Ar-H), 7.20 (dd,
1H, Ar-H), 7.45 (m, 2H, Ar-H), 7.50 (d, 1H, Ar-H). 13C
NMR (500 MHz, CDCl3) d in ppm: 162.72, 152.614,
142.362, 141.754, 135.630, 132.028, 131.898, 130.290,
128.341, 123.064, 120.892, 120.138, 87.035, 55.024,
47.270, 46.158. HRMS (EI): C18H19IN4 calcd: 418.07
found 418.065. Elemental Anal. calcd for C18H19IN4
were C, 51.69; H, 4.58; N, 13.39 found C, 52.02, H, 4.62;
N, 13.32.
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