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【结 构 式】

【分子编号】63707

【品名】1,1-dimethylethyl 3-{[3-methyl-2-(4-morpholinylcarbonyl)-1-benzofuran-4-yl]oxy}propyl(3-pyridinylmethyl)carbamate

【CA登记号】

【 分 子 式 】C28H35N3O6

【 分 子 量 】509.60252

【元素组成】C 65.99% H 6.92% N 8.25% O 18.84%

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:(VIII)

Alkaline hydrolysis of ester (I), followed by chlorination of the resulting carboxylic acid (II) by means of oxalyl chloride furnishes the acid chloride (III). This is then treated with morpholine (IV) to provide the corresponding amide (V). Displacement of the bromide group of (V) with 3-(aminomethyl)pyridine (VI) leads to the secondary amine (VII), which is further protected as the N-Boc derivative (VIII) employing di-tert-butyl dicarbonate. Addition of the 2-lithiated benzimidazole (IX) to the morpholine amide (VIII) gives rise to ketone (X). The N-Boc group of (X) is finally cleaved by treatment with trifluoroacetic acid in CH2Cl2.

1 Kawasaki, K.; Masubuchi, M.; Morikami, K.; Sogabe, S.; Aoyama, T.; Ebiike, H.; Niizuma, S.; Hayase, M.; Fujii, T.; Sakata, K.; Shindoh, H.; Shiratori, Y.; Aoki,Y.; Ohtsuka, T.; Shimma, N.; Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 3. Bioorg Med Chem Lett 2003, 13, 1, 87.
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) 51127 6-phenyl-1-(1-piperazinyl)-1-hexanone C16H24N2O 详情 详情
(II) 63703 4-[(3-bromopropyl)oxy]-3-methyl-1-benzofuran-2-carboxylic acid C13H13BrO4 详情 详情
(III) 63704 4-[(3-bromopropyl)oxy]-3-methyl-1-benzofuran-2-carbonyl chloride C13H12BrClO3 详情 详情
(IV) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(V) 63705 {4-[(3-bromopropyl)oxy]-3-methyl-1-benzofuran-2-yl}(4-morpholinyl)methanone C17H20BrNO4 详情 详情
(VI) 18731 3-pyridinylmethanamine; 3-pyridinylmethylamine 3731-52-0 C6H8N2 详情 详情
(VII) 63706 [3-methyl-4-({3-[(3-pyridinylmethyl)amino]propyl}oxy)-1-benzofuran-2-yl](4-morpholinyl)methanone C23H27N3O4 详情 详情
(VIII) 63707 1,1-dimethylethyl 3-{[3-methyl-2-(4-morpholinylcarbonyl)-1-benzofuran-4-yl]oxy}propyl(3-pyridinylmethyl)carbamate C28H35N3O6 详情 详情
(IX) 63708 [1-(2-propenyl)-1H-benzimidazol-2-yl]lithium C10H9LiN2 详情 详情
(X) 63709 1,1-dimethylethyl 3-[(3-methyl-2-{[1-(2-propenyl)-1H-benzimidazol-2-yl]carbonyl}-1-benzofuran-4-yl)oxy]propyl(3-pyridinylmethyl)carbamate C34H36N4O5 详情 详情
Extended Information