Salification method for 2-(6-quinolineamino)-6-cyclopropylamino-9H-purine
A technology of cyclopropylamino and quinolineamino, applied in the field of 2--6-cyclopropylamino-9H-purine salt formation, can solve the problems of large side effects and poor selectivity
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example 1
[0014] Example 1 Preparation of hydrochloride (compound II)
[0015] Add compound III (p is tetrahydropyranyl) (1.0g), tetrahydrofuran (20ml) and 6 N HCl (0.9ml) into a 50ml one-necked flask, stir, heat up to reflux, reflux for 1.5h, and analyze the reaction by TLC Completely, stop stirring, and cool to room temperature naturally. It was filtered, washed 3 times with acetone, and dried in vacuum at 40° C. for 6 h to obtain 0.9 g of a yellow solid.
[0016] Elemental analysis (C 17 h 15 N 7 • 2HCl) Found (calculated, %): C 52.11 (52.43), H 4.56 (4.37), N 25.60 (25.19), Cl 18.17 (17.97).
[0017] According to thermogravimetric analysis, this compound does not contain crystal water and decomposes at 280°C (determined by DTA).
[0018] 1 H-NMR (DMSO-d 6 , ppm) δ: 8.97 (2H, overlapped, 2 and 5 H on the quinoline ring), 8.90 (1H, d, J=8.1Hz, 4 H on the quinoline ring), 8.71 (1H, s, purine ring 8-position H), 8.30 (1H, dd, J=2.0, 9.3Hz, 7-position H on the quinoline ring), 8....
example 2
[0019] Example 2 prepares mesylate (compound II)
[0020] Add compound III (p is tetrahydropyranyl) (1.0g), acetone (6ml) and water (3ml) in 50ml one-necked flask, stir, heat up, add methanesulfonic acid (0.5ml), all solids dissolve , into a clear orange-yellow solution, about 10 minutes later, a yellow solid precipitated out, continued the reaction under reflux for 50 minutes, added water (3ml), the solids were all dissolved again, stopped stirring, and cooled to room temperature naturally. It was filtered, washed with acetone three times, and dried in vacuum at 40°C for 6 hours to obtain 1.2 g of a yellow solid.
[0021] Elemental analysis (C 17 h 15 N 7 ·2CH 3 SO 3 H) Found values (calculated, %): C 41.78 (41.79), H 5.03 (4.95), N 18.15 (17.96), S 11.94 (11.73).
[0022] Differential scanning calorimetry analysis shows that the compound contains crystal water, and thermogravimetric analysis shows that the water content is 6.64%, which confirms that the molecule cont...
example 3
[0026] Example 3 prepares hydrobromide (compound II)
[0027] Add compound III (p is tetrahydropyranyl) (1.0g), 6ml acetone and 3ml water in 50ml one-necked flask, stir, heat up, add 40% HBr (1.5ml), all solids dissolve, become clear After about 10 minutes, a yellow solid precipitated out of the orange solution. The reaction was continued for 50 minutes under reflux, and water (15ml) was added to dissolve the solid again. Stirring was stopped, and the mixture was naturally cooled to room temperature. It was filtered, washed with acetone three times, and dried in vacuum at 40°C for 6 hours to obtain 1.1 g of a yellow solid.
[0028] mp: >250°C.
[0029] 1 H-NMR (DMSO-d 6 , ppm) δ: 9.08 (1H, dd, J=1.6, 5.2Hz, 2-position H on the quinoline ring), 9.04 (1H, d, J=2.4Hz 5-position H on the quinoline ring), 8.94 (1H, d, J=8.4Hz, 4-position H on the quinoline ring), 8.80 (1H, s, 8-position H on the purine ring), 8.37 (1H, dd, J=2.4, 9.6Hz, 7-position H on the quinoline ring ), 8....
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