[3-methyl-4-({3-[(3-pyridinylmethyl)amino]propyl}oxy)-1-benzofuran-2-yl](4-morpholinyl)methanone -Drug Synthesis Database

【结构式】

【分子编号】63706

【品名】[3-methyl-4-({3-[(3-pyridinylmethyl)amino]propyl}oxy)-1-benzofuran-2-yl](4-morpholinyl)methanone

【CA登记号】

【分子式】C₂₃H₂₇N₃O₄

【分子量】409.4852

【元素组成】C 67.46% H 6.65% N 10.26% O 15.63%

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：(VII)

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.

参考文献中间体

合成目标

【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