methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate -Drug Synthesis Database

【结构式】

【分子编号】10258

【品名】methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate

【CA登记号】22813-31-6

【分子式】C₆H₇N₃O₄

【分子量】185.1394

【元素组成】C 38.93% H 3.81% N 22.7% O 34.57%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(III)

The condensation of 2-nitroimidazole (I) with methyl chloroacetate (II) by means of sodium methoxide in hot DMF gives methyl (2-nitro-1-imidazolyl)acetate (III), which is then treated with ethanolamine (IV) in methanol.

参考文献中间体

合成目标

【1】 Castaner, J.; Robinson, C.; Etanidazole. Drugs Fut 1995, 20, 8, 772.
【2】 Lee, W.W.; Brown, J.M.; Martinez, A.P.; Cory, M.J. (US Department of Health & Human Services); Nitroimidazoles of low toxicity and high activity as radiosensitizers of hypoxic tumor cells. US 4371540 .
【3】 Beaman, A.G.; Duschinsky, R.; Tautz, W.P. (F. Hoffmann-La Roche AG); 2-Nitroimidazoles. US 3679698 .
【4】 Beaman, A.G.; Duschinsky, R.; Tautz, W.P. (F. Hoffmann-La Roche AG); Novel imidazole derivs. and a process for the manufacture thereof. GB 1138529 .

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)	10145	2-Nitro-1H-imidazole; 2-Nitroimidazole	527-73-1	C₃H₃N₃O₂	详情	详情
(II)	10257	methyl 2-chloroacetate; methyl chloroacetate	96-34-4	C₃H₅ClO₂	详情	详情
(III)	10258	methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate	22813-31-6	C₆H₇N₃O₄	详情	详情
(IV)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The intermediate mixed anhydride (V) has been obtained as follows: the condensation of 2-nitroimidazole (I) with methyl 2-bromoacetate (II) by means of NaOMe in methanol gives 2-(2-nitro-1H-imidazol-1-yl)acetic acid methyl ester (III), which is hydrolyzed with NaOH to yield the corresponding acid (IV). Finally, this compound is condensed with isobutyl chloroformate by means of NMM in THF to afford the desired mixed anhydride intermediate (V). The condensation of 2,2,2-trifluoroacetaldehyde ethyl hemiacetal (VI) with nitromethane (VII) by means of K2CO3 gives 1,1,1-trifluoro-3-nitro-2-propanol (VIII), which is reduced with H2 over RaNi in ethanol to yield 3-amino-1,1,1-trifluoro-2-propanol (IX). Finally, this compound is condensed with the mixed anhydride intermediate (V) by means of NMM in THF to afford the target amide.

参考文献中间体

合成目标

【1】 Tracy, M.; Kelson, A.B.; Workman, P.; Lewis, A.D.; Aboagye, E.O. (Cancer Research UK; SRI International); Fluorinated 2-nitroimidazole analogs for detecting hypoxic tumor cells. EP 0775117; JP 1998506104; US 5721265; WO 9604249 .

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)	10145	2-Nitro-1H-imidazole; 2-Nitroimidazole	527-73-1	C₃H₃N₃O₂	详情	详情
(II)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情
(III)	10258	methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate	22813-31-6	C₆H₇N₃O₄	详情	详情
(IV)	56733	2-(2-nitro-1H-imidazol-1-yl)acetic acid		C₅H₅N₃O₄	详情	详情
(V)	56734			C₁₀H₁₃N₃O₆	详情	详情
(VI)	26582	1-ethoxy-2,2,2-trifluoro-1-ethanol	433-27-2	C₄H₇F₃O₂	详情	详情
(VII)	39563	nitromethane	75-52-5	CH₃NO₂	详情	详情
(VIII)	56735	1,1,1-trifluoro-3-nitro-2-propanol		C₃H₄F₃NO₃	详情	详情
(IX)	56736	3-amino-1,1,1-trifluoro-2-propanol	431-38-9	C₃H₆F₃NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

The condensation of 2-nitroimidazole (I) with methyl chloroacetate (II) by means of sodium methoxide in methanol - DMF at 150 C gives methyl 2-nitro-1-imidazolylacetate (III), which is then condensed with benzylamine (IV) in methanol.

参考文献中间体

合成目标

【1】 Castaner, J.; Roberts, P.J.; Benznidazole. Drugs Fut 1977, 2, 9, 568.
【2】 Beaman, A.G.; Duschinsky, R.; Tautz, W.P. (F. Hoffmann-La Roche AG); Novel imidazole derivs. and a process for the manufacture thereof. GB 1138529 .

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)	10145	2-Nitro-1H-imidazole; 2-Nitroimidazole	527-73-1	C₃H₃N₃O₂	详情	详情
(II)	10257	methyl 2-chloroacetate; methyl chloroacetate	96-34-4	C₃H₅ClO₂	详情	详情
(III)	10258	methyl 2-(2-nitro-1H-imidazol-1-yl)acetate; Methyl 2-nitro-1-imidazoleacetate	22813-31-6	C₆H₇N₃O₄	详情	详情
(IV)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情

Extended Information