Pyrazolo[3,4-d]pyrimidinone compounds and their application in the preparation of phosphodiesterase ⅸ inhibitors
A 4-d, pyrazolo technology, applied in the application field of pyrazolo [3, preparation of phosphodiesterase IX inhibitors, can solve the problems of low bioavailability, asymmetric synthesis, molecules containing hand shapes, etc. Achieve broad application prospects, easy operation, and low cost
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Embodiment 1
[0055] Embodiment one: the synthesis of compound W-1
[0056]
[0057] Formula (6)
[0058]In a 50mL round-bottom flask, add isopropanol (10mL), 1-(2-chlorophenyl)-6-chloro-pyrazolo[3,4-d]pyrimidin-4-one (0.4mmol, 0.1g), 2-amino-N-phenylpropanamide (0.48mmol, 0.08g), triethylamine (0.4mmol, 0.04g), and then heated to reflux, and the reaction was terminated after monitoring the completion of the reaction. After cooling to room temperature and concentrating, a colorless and transparent oil was obtained. The crude product was separated and purified by column chromatography (DCM:MeOH=25:1) to obtain 0.07 g of a white solid, with a yield of 41%.
[0059] 1 H NMR (300MHz, CDCl 3 )δ: 10.80(s, 1H), 8.64(br s, 1H), 8.13(s, 1H), 7.51-7.46(m, 2H), 7.35-7.24(m, 6H), 7.06(d, J=6.3 Hz, 2H), 4.56-4.49(m, 1H), 1.52(d, J=7.3Hz, 3H).ESI-MS: m / z=407[M-H] -
[0060] After identification, its structure is shown in formula (6).
Embodiment 2
[0061] Embodiment two: the synthesis of compound W-2
[0062]
[0063] Formula (7)
[0064] The synthesis method is the same as W-1, the raw materials are isopropanol (10mL), 1-(2-chlorophenyl)-6-chloro-pyrazolo[3,4-d]pyrimidin-4-one (0.4mmol, 0.1 g), 2-amino-N-(4-methoxyphenyl)propanamide (0.48mmol, 0.09g), triethylamine (0.4mmol, 0.04g). The crude product was separated and purified by column chromatography (DCM:MeOH=25:1) to obtain 0.08 g of a white solid with a yield of 45%.
[0065] 1 H NMR (300MHz, CDCl 3 )δ: 10.57(s, 1H), 8.14(s, 1H), 8.13(br s, 1H), 7.52-7.29(m, 4H), 7.11-6.77(m, 5H), 4.55-4.46(m, 1H ), 3.78(s, 3H), 1.52(d, J=6.9Hz, 3H) 13 C ESI-MS: m / z=437[M-H] - .
[0066] After identification, its structure is shown in formula (7).
Embodiment 3
[0067] Embodiment three: the synthesis of compound W-3
[0068]
[0069] Formula (8)
[0070] The synthesis method is the same as W-1, the raw materials are isopropanol (10mL), 1-phenyl-6-chloro-pyrazolo[3,4-d]pyrimidin-4-one (0.4mmol, 0.1g), 2- Amino-N-(4-methoxyphenyl)propanamide (0.48mmol, 0.09g), triethylamine (0.4mmol, 0.04g). The crude product was separated and purified by column chromatography (DCM:MeOH=25:1) to obtain 0.07 g of a white solid with a yield of 41%.
[0071] . 1 H NMR (300MHz, DMSO-d 6 )δ: 10.67(s, 1H), 10.17(br s, 1H), 8.06(d, J=6.3Hz, 3H), 7.54(d, J=9.0Hz, 2H), 7.36-7.23(m, 3H) , 7.11(d, J=6.3Hz, 1H), 6.89(d, J=9.0Hz, 2H), 4.55-4.46(m, 1H), 3.71(s, 1H).ESI-MS: m / z=403 [M-H] - .
[0072] After identification, its structure is shown in formula (8).
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