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【结 构 式】

【分子编号】18919

【品名】(1S,2S)-2-(cyclopropylamino)cyclohexanol

【CA登记号】

【 分 子 式 】C9H17NO

【 分 子 量 】155.24012

【元素组成】C 69.63% H 11.04% N 9.02% O 10.31%

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:(X)

OP C-33509 has been obtained by coupling imidazolecarboxamide (VI) with amine (IX) in refluxing CHCl3. The intermediates (VI) and (IX) have been obtained as follows: 1) Alkylation of 6-hydroxycarbostyril (I) with N-(3-bromopropyl)- phthalimide (II) in the presence of K2CO3 in DMF furnished the phthalimidopropyl ether (III). Subsequent hydrazinolysis of the phthalimide in refluxing EtOH provided the primary amine (IV). Then, the imidazolecarboxamide (VI) was obtained by treating amine (IV) with 1,1'-carbonyldiimidazole (V) and two equivalents of imidazole in DMSO. 2) Ring opening of 1,2 epoxycyclohexane (VII) with cyclopropylamine (VIII) gave the racemic trans aminoalcohol. Resolution of enantiomers (IX) and (X) was accomplished by esterification with (S)-mandelic acid (XI), followed by chromatographic separation of the diastereomeric esters. Hydrolysis of the desired ester (XII) then provided optically pure aminoalcohol (IX). Finally, the target urea derivative was obtained by coupling imidazolyl urea (VI) with amine (IX) in refluxing chloroform.

1 Koga, Y.; Kihara, Y.; Okada, M.; Inoue, Y.; Tochizawa, S.; Toga, K.; Tachibana, K.; Kimura, Y.; Nishi, T.; Hidaka, H.; 2(1H)- Quinoline derivatives as novel anti-arteriostenotic agents showing anti-thrombotic and anti-hyperplastic activities. Bioorg Med Chem Lett 1998, 8, 12, 1471.
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) 13913 6-Hydroxy-2(1H)-quinolinone C9H7NO2 详情 详情
(II) 15216 N-(3-Bromopropyl)phthalimide; 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione 5460-29-7 C11H10BrNO2 详情 详情
(III) 18912 2-[3-[(2-oxo-1,2-dihydro-6-quinolinyl)oxy]propyl]-1H-isoindole-1,3(2H)-dione C20H16N2O4 详情 详情
(IV) 18913 6-(3-aminopropoxy)-2(1H)-quinolinone C12H14N2O2 详情 详情
(V) 11353 1,1'-Carbonyldiimidazole; Di(1H-imidazol-1-yl)methanone; N,N-Carbonyldiimidazole; 1,1'-Carbonylbis(1H-imidazole) 530-62-1 C7H6N4O 详情 详情
(VI) 18915 N-[3-[(2-oxo-1,2-dihydro-6-quinolinyl)oxy]propyl]-1H-imidazole-1-carboxamide C16H16N4O3 详情 详情
(VII) 17986 7-oxabicyclo[4.1.0]heptane; cyclohexene oxide 286-20-4 C6H10O 详情 详情
(VIII) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(IX) 18918 (1R,2R)-2-(cyclopropylamino)cyclohexanol C9H17NO 详情 详情
(X) 18919 (1S,2S)-2-(cyclopropylamino)cyclohexanol C9H17NO 详情 详情
(XI) 12563 (2S)-2-Hydroxy-2-phenylethanoic acid; S-(+)-Mandelic acid 17199-29-0 C8H8O3 详情 详情
(XII) 18921 (1R,2R)-2-(cyclopropylamino)cyclohexyl (2S)-2-hydroxy-2-phenylethanoate C17H23NO3 详情 详情
Extended Information