To a stirred
suspension of 6-amino-3-methyl-3,4-dihydroquinazolin-2(1H)-one (11 ) (100 mg, 0.421 mmol, 1.0 equiv) in dichloromethane
(10 mL) was added pyridine (0.20 mL, 2.48 mmol, 5.9 equiv), followed
by 2-methoxybenzene-1-sulfonyl chloride (130 mg, 0.631 mmol, 1.5 equiv).
After 2 h, the solvent was evaporated and the residue was partitioned
between ethyl acetate and aqueous 2 M HCl. The organic layer was collected,
washed with water and brine, dried over magnesium sulfate, filtered,
and concentrated to a residue. The residue was dissolved in dimethyl
sulfoxide (DMSO, ∼1 mL) and purified by automated HPLC to provided
the desired material (50 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ 2.78 (s, 3H), 3.91 (s, 3H), 4.25
(s, 2H), 6.59 (d, J = 9.16 Hz, 1H), 6.79–6.81
(m, 2H), 6.97 (t, J = 7.5 Hz, 1H), 7.14 (d, J = 8.2 Hz, 1H), 7.52–7.56 (m, 1H), 7.68 (dd, J = 1.4, 7.8 Hz, 1H), 9.09 (s, 1H), 9.64 (s, 1H); HRMS [M
+ H] for C16H18N3O4S,
calcd 348.1013, found 348.1019; LCMS [M + H] = 384.1, >99% (t = 1.23 min).
suspension of 6-amino-3-methyl-3,4-dihydroquinazolin-2(1H)-one (
(10 mL) was added pyridine (0.20 mL, 2.48 mmol, 5.9 equiv), followed
by 2-methoxybenzene-1-sulfonyl chloride (130 mg, 0.631 mmol, 1.5 equiv).
After 2 h, the solvent was evaporated and the residue was partitioned
between ethyl acetate and aqueous 2 M HCl. The organic layer was collected,
washed with water and brine, dried over magnesium sulfate, filtered,
and concentrated to a residue. The residue was dissolved in dimethyl
sulfoxide (DMSO, ∼1 mL) and purified by automated HPLC to provided
the desired material (50 mg, 34%). 1H NMR (400 MHz, DMSO-d6) δ 2.78 (s, 3H), 3.91 (s, 3H), 4.25
(s, 2H), 6.59 (d, J = 9.16 Hz, 1H), 6.79–6.81
(m, 2H), 6.97 (t, J = 7.5 Hz, 1H), 7.14 (d, J = 8.2 Hz, 1H), 7.52–7.56 (m, 1H), 7.68 (dd, J = 1.4, 7.8 Hz, 1H), 9.09 (s, 1H), 9.64 (s, 1H); HRMS [M
+ H] for C16H18N3O4S,
calcd 348.1013, found 348.1019; LCMS [M + H] = 384.1, >99% (t = 1.23 min).
