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【结 构 式】

【分子编号】23949

【品名】N2-Nitroguanidine

【CA登记号】

【 分 子 式 】CH4N4O2

【 分 子 量 】104.06852

【元素组成】C 11.54% H 3.87% N 53.84% O 30.75%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IX)

The reaction of 2-chloro-4-cyanopyridine (I) with sodium methoxide in refluxing methanol gives 2-methoxy-4-cyanopyridine (II), which by reduction with H2 over Raney-Ni and semicarbazide HCl in water-ethanol is converted to 2-methoxypyridine-4-carboxyaldehyde (III). The condensation of (III) with malonic acid (IV) by means of piperidine in hot pyridine yields 3-(2-methoxy-4-pyridyl)acrylic acid (V), which is esterified with ethanol and H2SO4 to the ethyl ester (VI). The reduction of (VII) with H2 over Pd/C in ethanol affords the corresponding propionate (VII). Formylation of (VII) with ethyl formate and NaH gives ethyl 2-formyl-3-(2-methoxy-4-pyridyl)propionate (VIII), which is cyclized with nitroguanidine (IX) by means of sodium methoxide in refluxing methanol yielding 2-nitroamino-5-12-methoxy-4-pyridylmethylpyrimidin-4(1H)-one (X). The reaction of (X) with 2-[5-(dimethylaminomethyl)-2 furylmethylthio]ethylamine in refluxing ethanol gives the O-methyl derivative of SK&F 93574 (XII), whicn is finally deprotected with HCl in refluxing ethanol.

1 Brown, T.H.; Ife, R.J. (SmithKline Beecham plc); Pyrimidine compounds. DD 140252; EP 0003677; ES 477667; US 4234588; US 4649141 .
2 Adger, B.M.; Lewis, N.J. (SmithKline Beecham plc); Chemical process. EP 0141560 .
3 Prous, J.; Castaner, J.; SK&F-93574. Drugs Fut 1986, 11, 8, 671.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 23944 1-Hydrazinecarboxamide 563-41-7 CH5N3O 详情 详情
(I) 23940 2-Chloro-4-pyridinecarbonitrile; 2-chloroisonicotinonitrile 33252-30-1 C6H3ClN2 详情 详情
(II) 23943 2-methoxyisonicotinonitrile C7H6N2O 详情 详情
(III) 23941 2-methoxyisonicotinaldehyde C7H7NO2 详情 详情
(IV) 12963 Malonic acid 141-82-2 C3H4O4 详情 详情
(V) 23945 (Z)-3-(2-methoxy-4-pyridinyl)-2-propenoic acid C9H9NO3 详情 详情
(VI) 23946 ethyl (Z)-3-(2-methoxy-4-pyridinyl)-2-propenoate C11H13NO3 详情 详情
(VII) 23947 ethyl 3-(2-methoxy-4-pyridinyl)propanoate C11H15NO3 详情 详情
(VIII) 23948 ethyl 2-formyl-3-(2-methoxy-4-pyridinyl)propanoate C12H15NO4 详情 详情
(IX) 23949 N2-Nitroguanidine CH4N4O2 详情 详情
(X) 23950 5-(2-Methoxypyridin-4-yl)-2-(nitroamino)pyrimidin-4(1H)-one C11H11N5O4 详情 详情
(XI) 13851 2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]-1-ethanamine; N-[(5-[[(2-Aminoethyl)sulfanyl]methyl]-2-furyl)methyl]-N,N-dimethylamine C10H18N2OS 详情 详情
(XII) 23951 2-([2-[([5-[(dimethylamino)methyl]-2-furyl]methyl)sulfanyl]ethyl]amino)-5-[(2-methoxy-4-pyridinyl)methyl]-4(1H)-pyrimidinone C21H27N5O3S 详情 详情
Extended Information