4,5-dichloro-3(2H)-pyridazinone -Drug Synthesis Database

【结构式】

【分子编号】24570

【品名】4,5-dichloro-3(2H)-pyridazinone

【CA登记号】

【分子式】C₄H₂Cl₂N₂O

【分子量】164.97816

【元素组成】C 29.12% H 1.22% Cl 42.98% N 16.98% O 9.7%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

The condensation of 2-glycidyloxy-1-chlorobenzene (I) with ethylenediamine (II) in refluxing ethanol gives N-[3-(2-chlorophenoxy)-2-hydroxy propyl]ethylenediamine (III), which is then condensed with 4,5-dichloropyridazinone (IV) in refluxing ethanol.

参考文献中间体

合成目标

【1】 Raabe, T.; Bohn, H.; Martorana, P.A.; Nitz R.-E. (Cassella AG); N-phenoxypropanol-N'-pyridazinyl ethylendiamines as beta -receptor blockers. DD 202013; DE 3048487; EP 54946; JP 57128677; US 4532239 .
【2】 Castaner, J.; Prous, J.; Ridazolol. Drugs Fut 1986, 11, 12, 1044.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24567	2-[(2-chlorophenoxy)methyl]oxirane		C₉H₉ClO₂	详情	详情
(II)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(III)	24569	1-[(2-aminoethyl)amino]-3-(2-chlorophenoxy)-2-propanol		C₁₁H₁₇ClN₂O₂	详情	详情
(IV)	24570	4,5-dichloro-3(2H)-pyridazinone		C₄H₂Cl₂N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Pyridazinone (I) was converted to 3,4,5-trichloropyridazine (VIII) on treatment with POCl3. Nucleophylic substitution in (II) with 3-aminopropanol (III) gave, after crystallization, the desired isomer (IV). Hydrolysis of the 3-chloro group of (IV) was carried out with AcOH and AcONa, resulting in the N,O-diacetyl derivative (V). Subsequent reaction of (V) with aqueous HBr provided bromide (VI), which was then treated with N-methyl homoveratrylamine (VII) to furnish the target compound (VIII). This compound was finally isolated as the fumarate salt on treatment with fumaric acid in EtOH (1).

参考文献中间体

合成目标

【1】 Kotay-Nagy, P.; et al.; A new synthesis of EGIS-7229, a potent antiarrhythmic drug-candidate. 15th European Federation for Medicinal Chemistry International Symposium on Medicinal Chemistry (Sept 6 1998, Edinburgh) 1998, Abst P.151.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	24570	4,5-dichloro-3(2H)-pyridazinone		C₄H₂Cl₂N₂O	详情	详情
(II)	27529	3,4,5-trichloropyridazine	14161-11-6	C₄HCl₃N₂	详情	详情
(III)	18522	3-amino-1-propanol	156-87-6	C₃H₉NO	详情	详情
(IV)	27530	3-[(3,5-dichloro-4-pyridazinyl)amino]-1-propanol		C₇H₉Cl₂N₃O	详情	详情
(V)	27531	3-[acetyl(5-chloro-3-oxo-2,3-dihydro-4-pyridazinyl)amino]propyl acetate		C₁₁H₁₄ClN₃O₄	详情	详情
(VI)	27532	4-[(3-bromopropyl)amino]-5-chloro-3(2H)-pyridazinone		C₇H₉BrClN₃O	详情	详情
(VII)	18938	2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine	3490-06-0	C₁₁H₁₇NO₂	详情	详情
(VIII)	27533	5-chloro-4-([3-[(3,4-dimethoxyphenethyl)(methyl)amino]propyl]amino)-3(2H)-pyridazinone		C₁₈H₂₅ClN₄O₃	详情	详情
(IX)	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情

Extended Information