Water → HCID 18361815, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(5-methylisoxazol-3-yl)-6-(1,2,4-triazol-3-yl)methyloxy-1,2,4-triazolo[3,4-a]phthalazine (100 mg, 0.29 mmol) in N,N-dimethylformamide (6 ml) at room temperature under nitrogen was added sodium hydride (17 mg, 0.41 mmol). The mixture was cooled to 0° C. and 2-iodopropane (0.04 ml, 0.36 mmol) added after 0.25 h. The mixture was left to stir at room temperature overnight, water was added and the precipitate filtered off. The crude product was flash chromatographed on silica gel, eluting with ethyl acetate→4% methanol/ethyl acetate, to give the title-product (25 mg, 22%), mp 179-181° C.; 1H NMR (360 MHz, CDCl3) δ 1.58 (6H, d, J=6.7 Hz, 2 of CH3), 2.59 (3H, s, CH3), 4.58 (1H, septet, J=6.7 Hz, CH), 5.72 (2H, s, CH2), 7.01 (1H, s, Ar—H), 7.78 (1H, t, J=7.2 Hz, Ar—H), 7.94 (1H, t, J=7.6 Hz, Ar—H), 8.13 (1H, s, Ar—H), 8.28 (1H, d, J=7.9 Hz, Ar—H), 8.80 (1H, d, J=7.4 Hz, Ar—H); MS (ES30) m/e 391 [MH]+; Anal. Found. C, 56.81; H, 4.68; N, 27.89; C19H18N8O2.0.7H2O requires C, 56.62; H, 4.85; N, 27.80%.

Provenance & Evidence