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【结 构 式】

【分子编号】20958

【品名】3(2H)-pyridazinone

【CA登记号】

【 分 子 式 】C4H4N2O

【 分 子 量 】96.08864

【元素组成】C 50% H 4.2% N 29.15% O 16.65%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(III)

Title compound can be prepared as shown in Scheme: 1) 3,6-Dichloropyridazine (I) is converted to 3(2H)-pyridazinone (III) in two steps. 2) 3-N-(2-Benzo[1,4]dioxanylmethyl)amino-1-propanol (V), obtained by the reaction of (2-benzo[1,4]dioxanylmethyl)-4-toluenesulfonate (IV) with 3-amino-1-propanol, is N-benzylated to form the N-protected amino alcohol (VI), which on treatment with thionyl chloride affords the chloroalkyl derivative (VII). 3) Alkylation of 3(2H)-pyridazinone (III) with (VII) under phase-transfer catalysis conditions to the N-benzylated GYKI-12743 (VIII) and then removal of the N-benzyl group by hydrogenation gives GYKI-12743.

1 Kasztreiner, E.; Rabloczky, G.; Makk, N.; Jaszlits, L.; Matyus, P.; Cseh, G.; Pribusz, geb. Rapp, I.; Czakó, K.; Diesler, E.; Elekes, I.; Kaufer, L.; Kuhár, geb. Kürthy, M.; Kincsessy, J.; Kosáry, J.; Nagy, Gyöngyi geb. C. (Richter Gedeon Vegyeszeti); 3(2H)-Pyridazinone derivs., a process and intermediates for preparing them and medicaments containing them and/or other 3(2H)-pyridazinone derivatives. AU 8664496; EP 0220735; JP 87161768 .
2 Kasztreiner, E.; Matyus, P.; Rabloczky, G.; Jaszlits, L.; GYKI-12743. Drugs Fut 1989, 14, 7, 622.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
18522 3-amino-1-propanol 156-87-6 C3H9NO 详情 详情
19171 1-(Chloromethyl)benzene; Benzyl chloride 100-44-7 C7H7Cl 详情 详情
(I) 11292 3,6-Dichloropyridazine 141-30-0 C4H2Cl2N2 详情 详情
(II) 20957 6-chloro-3(2H)-pyridazinone C4H3ClN2O 详情 详情
(III) 20958 3(2H)-pyridazinone C4H4N2O 详情 详情
(IV) 20959 2,3-dihydro-1,4-benzodioxin-2-ylmethyl 4-methylbenzenesulfonate C16H16O5S 详情 详情
(V) 20960 3-[(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)amino]-1-propanol C12H17NO3 详情 详情
(VI) 20961 3-[benzyl(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)amino]-1-propanol C19H23NO3 详情 详情
(VII) 20962 N-benzyl-3-chloro-N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-1-propanamine; N-benzyl-N-(3-chloropropyl)-N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)amine C19H22ClNO2 详情 详情
(VIII) 20963 2-[3-[benzyl(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)amino]propyl]-3(2H)-pyridazinone C23H25N3O3 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XII)

The pyridazinone intermediate (XII) was prepared from dihydroxypyridazine (IX) in three synthetic steps.

1 Matyus, P.; GYKI-16084. Drugs Fut 1999, 24, 10, 1072.
2 3(2H)-Pyridazinone derivs. and pharmaceutical compsns. containing these cpds.. WO 9638441 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 28717 3,6-pyridazinediol 123-33-1 C4H4N2O2 详情 详情
(X) 11292 3,6-Dichloropyridazine 141-30-0 C4H2Cl2N2 详情 详情
(XI) 20957 6-chloro-3(2H)-pyridazinone C4H3ClN2O 详情 详情
(XII) 20958 3(2H)-pyridazinone C4H4N2O 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XII)

Finally, N-alkylation of the potassium salt of (XII) with the base form of (VIII) was performed in dimethyl sulfoxide to afford GYKI-16084.

1 Matyus, P.; GYKI-16084. Drugs Fut 1999, 24, 10, 1072.
2 3(2H)-Pyridazinone derivs. and pharmaceutical compsns. containing these cpds.. WO 9638441 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 28716 3-chloro-N-[(2R)-2,3-dihydro-1,4-benzodioxin-2-ylmethyl]-1-propanamine C12H16ClNO2 详情 详情
(XII) 20958 3(2H)-pyridazinone C4H4N2O 详情 详情
Extended Information