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【结 构 式】 
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【分子编号】24199 【品名】Ethyl carbamate; Urethane 【CA登记号】51-79-6 |
【 分 子 式 】C3H7NO2 【 分 子 量 】89.09412 【元素组成】C 40.44% H 7.92% N 15.72% O 35.92% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of chloranil (I) with ethyl carbamate (II) by means of Na in dry benzene gives 2,5-dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone (III), which is then condensed with aziridine (IV) by means of triethylamine in THF.
| 【1】 Driscoll, J.S.; et al.; Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother Rep 1974, 4, 2, 1. |
| 【2】 Zubrod, C.G.; Rall, D.P.; Anu Rev Pharmacol 1962, 2, 109. |
| 【3】 Kahn, A.H.; Driscoll, J.S.; Potential central nervous system antitumor agents. Azirinylbenzoquinones. 1. J Med Chem 1976, 19, 2, 313-317. |
| 【4】 Driscoll, J.S.; et al. (US Department of Health & Human Services); Aziridinyl quinone anti-transplanted tumor agents. US 4146622 . |
| 【5】 Cabanillas, F.; Blancafort, P.; Serradell, M.N.; Castaner, J.; AZQ. Drugs Fut 1981, 6, 6, 338. |
| 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) | 21891 | 2,3,5,6-Tetrachloro-1,4-benzoquinone; 2,3,5,6-Tetrachlorobenzo-1,4-quinone; p-Chloranil | 118-75-2 | C6Cl4O2 | 详情 | 详情 |
| (II) | 24199 | Ethyl carbamate; Urethane | 51-79-6 | C3H7NO2 | 详情 | 详情 |
| (III) | 32193 | 2,5-Dichloro-3,6-bis(ethoxycarbonylamino)-1,4-benzoquinone; Ethyl 2,5-dichloro-4-[(ethoxycarbonyl)amino]-3,6-dioxo-1,4-cyclohexadien-1-ylcarbamate | C12H12Cl2N2O6 | 详情 | 详情 | |
| (IV) | 10151 | Ethyleneimine; Aziridine; Azirane | 151-56-4 | C2H5N | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)By an ester-exchange reaction between 2-phenylpropane 1 3-diol (I) in ethyl carbamate (II).
| 【1】 Ludwig, B.J.; et al.; Carbamate derivatives related to meprobamate. J Med Chem 1969, 12, 3, 462. |
| 【2】 Prous, J.; Castaner, J.; Felbamate. Drugs Fut 1986, 11, 11, 931. |
合成路线3
该中间体在本合成路线中的序号：(II)Cyanoacetic acid (I) is condensed with urethane (II) in hot Ac2O to afford N ethoxycarbonyl-cyanoacetamide (III). Subsequent reaction of (III) with triethyl orthoformate yields alpha-cyano-beta-ethoxy-N-ethoxycarbonyl-acrylamide (IV). The ethoxy group of (IV) is then displaced with hydrazine hydrate in EtOH to produce the hydrazino acrylamide (V). Finally, thermal cyclization of (V) gives rise to the title pyrazolopyrimidine (1, 2).
| 【1】 Hildick, B.G.; Shaw, G.; Purines, pyrimidines, and imidazoles. Part XXXVII. Some new syntheses of pyrazolo[3,4-d]pyrimidines, including allopurinol. J Chem Soc 1971, 9, 1610. |
| 【2】 Shaw, G.; Baildon, S.; Lees, P. Sr.; Process for the preparation of biologically active cpds. as well as novel cpds.. DE 1814082 . |
| 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) | 12591 | Cyanoacetic Acid; 2-Cyanoacetic acid | 372-09-8 | C3H3NO2 | 详情 | 详情 |
| (II) | 24199 | Ethyl carbamate; Urethane | 51-79-6 | C3H7NO2 | 详情 | 详情 |
| (III) | 48249 | ethyl 2-cyanoacetylcarbamate | C6H8N2O3 | 详情 | 详情 | |
| (IV) | 63576 | ethyl (E)-2-cyano-3-ethoxy-2-propenoylcarbamate | C9H12N2O4 | 详情 | 详情 | |
| (V) | 63577 | ethyl (E)-2-cyano-3-hydrazino-2-propenoylcarbamate | C7H10N4O3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(A)The condensation of 2-amino-4-methylbenzophenone (I) with isopropyl iodide (II) by means of sodium carbonate gives 4-methyl-2-isopropylaminobenzophenone (III), which is the cyclized with urethane (A) under the catalytic action of ZnCl2 at 190 C.
| 【1】 Castañer, J.; Thorpe, P.; Proquazone. Drugs Fut 1976, 1, 11, 540. |
| 【2】 Ott, H.; Denzer, M.; o-Isopropylaminobenzophenones. DE 180550,1; FR 2002598; GB 1248428 . |