2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate -Drug Synthesis Database

【结构式】

【分子编号】33962

【品名】2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate

【CA登记号】

【分子式】C₂₈H₂₄ClNO₆

【分子量】505.9544

【元素组成】C 66.47% H 4.78% Cl 7.01% N 2.77% O 18.97%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

1) By condensation of 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic acid (II) with benzyl bromoacetate (A) by means of K2CO3 in DMF. 2) By cyclocondensation of a mixture of N-(p-methoxyphenyl)-N-(p-chlorobenzoyl)hydrazine (III) and benzyl levulinate (IV) at 80 C in acetic acid.

参考文献中间体

合成目标

【1】 Boltze, K.; Brendler, O.; Dell, H.-D.; Jacobi, H.; Novel substituted indole compound, process for the preparation and therapeutic compositions containing it.. DE 2234651; ES 416877; FR 2192828; JP 49043970; US 3910952 .
【2】 Leeson, P.A.; Castaner, J.; Acemetacin. Drugs Fut 1977, 2, 7, 423.

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)	12869	benzyl 2-bromoacetate	5437-45-6	C₉H₉BrO₂	详情	详情
(I)	33962	2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate		C₂₈H₂₄ClNO₆	详情	详情
(II)	22930	2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid		C₁₉H₁₆ClNO₄	详情	详情
(III)	24319	4-chloro-N-(4-methoxyphenyl)benzohydrazide		C₁₄H₁₃ClN₂O₂	详情	详情
(IV)	33963	2-(benzyloxy)-2-oxoethyl 4-oxopentanoate		C₁₄H₁₆O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

3) The reaction of p-methoxyphenylhydrazine (V) with benzyl levulinate (IV) in acetic acid gives the corresponding hydrazone (VI), which, without isolation, is cyclized to benzyl 5-methoxy-2-methylindole-3-acetoxyacetate (VII) at 80 C in acetic acid. Then this compound is benzoylated with p-chlorobenzoyl chloride (B) by means of NaH in DMF. 4) The hydrazone (VI) can also be benzoylated first giving the corresponding hydrazone (VIII), which is then cyclized at 80 C in acetic acid.

参考文献中间体

合成目标

【1】 Boltze, K.; Brendler, O.; Dell, H.-D.; Jacobi, H.; Novel substituted indole compound, process for the preparation and therapeutic compositions containing it.. DE 2234651; ES 416877; FR 2192828; JP 49043970; US 3910952 .
【2】 Leeson, P.A.; Castaner, J.; Acemetacin. Drugs Fut 1977, 2, 7, 423.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(B)	10295	p-Chlorobenzoyl chloride; 4-Chlorobenzoyl chloride	122-01-0	C₇H₄Cl₂O	详情	详情
(I)	33962	2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate		C₂₈H₂₄ClNO₆	详情	详情
(IV)	33963	2-(benzyloxy)-2-oxoethyl 4-oxopentanoate		C₁₄H₁₆O₅	详情	详情
(V)	12688	4-Hydrazinophenyl methyl ether; 1-(4-Methoxyphenyl)hydrazine	3471-32-7	C₇H₁₀N₂O	详情	详情
(VI)	33964	2-(benzyloxy)-2-oxoethyl 4-[(Z)-2-(4-methoxyphenyl)hydrazono]pentanoate		C₂₁H₂₄N₂O₅	详情	详情
(VII)	33966	2-(benzyloxy)-2-oxoethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate		C₂₁H₂₁NO₅	详情	详情
(VIII)	33965	2-(benzyloxy)-2-oxoethyl 4-[(Z)-2-(4-chlorobenzoyl)-2-(4-methoxyphenyl)hydrazono]pentanoate		C₂₈H₂₇ClN₂O₆	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

The condensation of 2-aminomethylpyridine (II) with 2,2,2-trifluoroethyl-2,5-bis(2,2,2-trifluoroethoxy)benzoate (I) in refluxing glyme gives 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-pyridylmethyl)benzamide (III), which is then hydrogenated with H2 over Pd/C in acetic acid.

参考文献中间体

合成目标

【1】 Bannitt, E.H.; Bronn, W.R.; Derivatives of pyrrolidine and piperidine. ES 435870; FR 2265366; GB 1508015; JP 58065268; US 3900481 .
【2】 Hillier, K.; Castaner, J.; Flecainide acetate. Drugs Fut 1977, 2, 9, 586.

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)	33962	2-(benzyloxy)-2-oxoethyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate		C₂₈H₂₄ClNO₆	详情	详情
(II)	13582	2-Pyridinylmethanamine; 2-Pyridinylmethylamine; 2-(Aminomethyl)pyridine	3731-51-9	C₆H₈N₂	详情	详情
(III)	33970	N-(2-pyridinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide		C₁₇H₁₄F₆N₂O₃	详情	详情

Extended Information