N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】36536

【品名】N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide

【CA登记号】154594-15-7

【分子式】C₁₀H₁₀N₄O

【分子量】202.21576

【元素组成】C 59.4% H 4.98% N 27.71% O 7.91%

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：(III)

Catalytic hydrogenation of 4-nitroacetanilide (I) afforded aniline (II), which was condensed with N,N-dimethylformamide azine to produce the triazolyl derivative (III). Acid hydrolysis of the acetamido group gave rise to amine (IV). Then, diazotization, followed by stannous chloride reduction of the diazonium salt, furnished the intermediate hydrazine (V).

参考文献中间体

合成目标

【1】 Matassa, V.G.; Pengilley, R.R.; Russell, M.G.N.; et al.; 3-[3-(Piperidin-1-yl)propyl]indoles as highly selective h5-HT1D receptor agonists. J Med Chem 1999, 42, 24, 4981.
【2】 Baker, R.; Bourrain, S.; Castro Pineiro, J.L.; Chambers, M.S.; Guiblin, A.R.; Hobbs, S.C.; Jelley, R.A.; Madin, A.; Matassa, V.G.; Reeve, A.J.; Russell, M.G.N.; Showell, G.A.; Sternfeld, F.; Street, L.J.; Van Niel, M.B. (Merck Sharp & Dohme Ltd.); Azetidine, pyrrolidine and piperidine derivs.. EP 0804434; JP 1998503768; US 5854268; WO 9604274 .

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)	36535	N-(4-nitrophenyl)acetamide	104-04-1	C₈H₈N₂O₃	详情	详情
(II)	29016	N-(4-aminophenyl)acetamide	122-80-5	C₈H₁₀N₂O	详情	详情
(III)	36536	N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide	154594-15-7	C₁₀H₁₀N₄O	详情	详情
(IV)	36537	4-(4H-1,2,4-triazol-4-yl)phenylamine; 4-(4H-1,2,4-triazol-4-yl)aniline		C₈H₈N₄	详情	详情
(V)	25647	4-(4-hydrazinophenyl)-4H-1,2,4-triazole		C₈H₉N₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Hydrogenation of p-nitroacetanilide (I) over Pd/C afforded p-aminoacetanilide (II), which was converted to triazolylacetanilide (III) upon treatment with N,N-dimethylformamide azine and p-toluenesulfonic acid. Acid hydrolysis of the acetamide (III) provided triazolylaniline (IV). Subsequent diazotization of (IV), followed by SnCl2 reduction of the diazonium salt furnished hydrazine (V). Fischer indole synthesis employing (V) and dihydropyran (VI) gave rise to the indolylpropanol (VII), which was converted to the intermediate mesylate (VIII) using CH3SO2Cl and Et3N.

参考文献中间体

合成目标

【1】 Stanton, J.A.; Showell, G.A.; Neduvelil, J.G.; Bourrain, S.; Beer, M.S.; MacLeod, A.M.; 4-Hydroxy-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperidines: Selective h5-HT1D agonists for the treatment of migraine. Bioorg Med Chem Lett 1999, 9, 23, 3369.
【2】 Baker, R.; Bourrain, S.; Castro Pineiro, J.L.; Chambers, M.S.; Guiblin, A.R.; Hobbs, S.C.; Jelley, R.A.; Madin, A.; Matassa, V.G.; Reeve, A.J.; Russell, M.G.N.; Showell, G.A.; Sternfeld, F.; Street, L.J.; Van Niel, M.B. (Merck Sharp & Dohme Ltd.); Azetidine, pyrrolidine and piperidine derivs.. EP 0804434; JP 1998503768; US 5854268; WO 9604274 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	40722	N'-[(E)-(dimethylamino)methylidene]-N,N-dimethylhydrazonoformamide		C₆H₁₄N₄	详情	详情
(I)	36535	N-(4-nitrophenyl)acetamide	104-04-1	C₈H₈N₂O₃	详情	详情
(II)	29016	N-(4-aminophenyl)acetamide	122-80-5	C₈H₁₀N₂O	详情	详情
(III)	36536	N-[4-(4H-1,2,4-triazol-4-yl)phenyl]acetamide	154594-15-7	C₁₀H₁₀N₄O	详情	详情
(IV)	36537	4-(4H-1,2,4-triazol-4-yl)phenylamine; 4-(4H-1,2,4-triazol-4-yl)aniline		C₈H₈N₄	详情	详情
(V)	25647	4-(4-hydrazinophenyl)-4H-1,2,4-triazole		C₈H₉N₅	详情	详情
(VI)	13684	3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran	110-87-2	C₅H₈O	详情	详情
(VII)	36538	3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]-1-propanol		C₁₃H₁₄N₄O	详情	详情
(VIII)	36539	3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl methanesulfonate		C₁₄H₁₆N₄O₃S	详情	详情

Extended Information