3-(1H-pyrazol-5-yl)benzaldehyde -Drug Synthesis Database

【结构式】

【分子编号】17996

【品名】3-(1H-pyrazol-5-yl)benzaldehyde

【CA登记号】

【分子式】C₁₀H₈N₂O

【分子量】172.1864

【元素组成】C 69.76% H 4.68% N 16.27% O 9.29%

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：(V)

Condensation of 3-acetylbenzonitrile (I) with N,N-dimethylformamide dimethylacetal (II) at 90 C provided enaminoketone (III). Reaction of (III) with hydrazine acetate in methanol generated pyrazole (IV), and then, reduction of nitrile group with Raney Nickel in aqueous formic acid gave aldehyde (V). Condensation of this aldehyde with benzylamine (VI) in refluxing toluene, followed by reduction of the intermediate imine (VII) with ethanolic NaBH4 yielded secondary amine (VIII). Finally, the target urea was obtained by condensation of amine (VIII) with phenyl N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]carbamate in the presence of triethylamine.

参考文献中间体

合成目标

【1】 Tanaka, A.; et al.; Inhibitors of acyl-CoA:cholesterol O-acyltransferase. 2. Identification and structure-activity relationships of a novel series of N-alkyl-N-(heteroaryl-substituted benzyl)-N'-arylureas. J Med Chem 1998, 41, 12, 2390-2410.

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)	17992	m-Cyanoacetophenone; 3-acetylbenzonitrile	6136-68-1	C₉H₇NO	详情	详情
(III)	17994	3-[(E)-3-(dimethylamino)-2-propenoyl]benzonitrile		C₁₂H₁₂N₂O	详情	详情
(IV)	17995	3-(1H-pyrazol-5-yl)benzonitrile		C₁₀H₇N₃	详情	详情
(V)	17996	3-(1H-pyrazol-5-yl)benzaldehyde		C₁₀H₈N₂O	详情	详情
(VII)	17998	N-benzyl-N-[(E)-[3-(1H-pyrazol-5-yl)phenyl]methylidene]amine; phenyl-N-[(E)-[3-(1H-pyrazol-5-yl)phenyl]methylidene]methanamine		C₁₇H₁₅N₃	详情	详情
(VIII)	17999	N-benzyl[3-(1H-pyrazol-5-yl)phenyl]methanamine; N-benzyl-N-[3-(1H-pyrazol-5-yl)benzyl]amine		C₁₇H₁₇N₃	详情	详情
(IX)	18000	phenyl 6-methyl-2,4-bis(methylsulfanyl)-3-pyridinylcarbamate		C₁₅H₁₆N₂O₂S₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Condensation of chloropyridine (I) with cyclooctylamine (II) provided the cyclooctylaminopyridine (III). The aminonitroethylene derivative (VI) was prepared by reaction of 1,1-bis(methylsulfanyl)-2-nitroethylene (IV) with cyclohexylamine (V) in refluxing EtOH. Subsequent condensation of this intermediate with the sodium salt of sulfonamide (III) yielded the title compound.

参考文献中间体

合成目标

【1】 Masereel, B.; Wouters, J.; Pochet, L.; Lambert, D.; Design, synthesis, and anticonvulsant activity of 1-(pyrid-3-ylsulfonamido)-2-nitroethylenes. J Med Chem 1998, 41, 17, 3239.

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)	22151	4-chloro-3-pyridinesulfonamide		C₅H₅ClN₂O₂S	详情	详情
(II)	17996	3-(1H-pyrazol-5-yl)benzaldehyde		C₁₀H₈N₂O	详情	详情
(II)	22152	cyclooctanamine; cyclooctylamine	5452-37-9	C₈H₁₇N	详情	详情
(III)	22153	4-(cyclooctylamino)-3-pyridinesulfonamide		C₁₃H₂₁N₃O₂S	详情	详情
(VI)	13853	Methyl 1-(methylsulfanyl)-2-nitrovinyl sulfide; 1,1-Bis(methylthio)-2-nitroethylene; 1,1-Bis(methylsulfanyl)-2-nitroethylene	13623-94-4	C₄H₇NO₂S₂	详情	详情
(VI)	22156	N-[(E)-1-(methylsulfanyl)-2-nitroethenyl]cyclohexanamine; N-cyclohexyl-N-[(E)-1-(methylsulfanyl)-2-nitroethenyl]amine		C₉H₁₆N₂O₂S	详情	详情

Extended Information