1-(chloromethyl)-4-isopropylbenzene -Drug Synthesis Database

【结构式】

【分子编号】33769

【品名】1-(chloromethyl)-4-isopropylbenzene

【CA登记号】2051-18-5

【分子式】C₁₀H₁₃Cl

【分子量】168.66592

【元素组成】C 71.21% H 7.77% Cl 21.02%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Alkylation of 5-nitroindole (I) with 4-isopropylbenzyl chloride (II) in the presence of Cs2CO3 provided the N-benzylindole derivative (III). Reduction of the nitro group of (III) by hydrogenation over Pd/C gave the corresponding amine, which was isolated as the hydrochloride salt (IV). The required pyrroloquinazoline system (V) was then prepared by reaction of (IV) with trichloromethyl isocyanate, followed by treatment with POCl3. Displacement of the 1-chlorine of (V) by ammonia afforded amine (VI). The remaining 3-chlorine of (VI) was then displaced by cyclopropylamine (VII) to furnish the title compound.

参考文献中间体

合成目标

【1】 Boykow, G.; Ahn, H.-S.; Arik, L.; et al.; Structure-activity relationships of pyrroloquinazolines as thrombin receptor antagonists. Bioorg Med Chem Lett 1999, 9, 14, 2073.

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)	26916	5-Nitroindole; 5-nitro-1H-indole	6146-52-7	C₈H₆N₂O₂	详情	详情
(II)	33769	1-(chloromethyl)-4-isopropylbenzene	2051-18-5	C₁₀H₁₃Cl	详情	详情
(III)	33770	1-(4-isopropylbenzyl)-5-nitro-1H-indole		C₁₈H₁₈N₂O₂	详情	详情
(IV)	33771	1-(4-isopropylbenzyl)-1H-indol-5-amine; 1-(4-isopropylbenzyl)-1H-indol-5-ylamine		C₁₈H₂₀N₂	详情	详情
(V)	33772	1,3-dichloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazoline		C₂₀H₁₇Cl₂N₃	详情	详情
(VI)	33773	3-chloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazolin-1-ylamine; 3-chloro-7-(4-isopropylbenzyl)-7H-pyrrolo[3,2-f]quinazolin-1-amine		C₂₀H₁₉ClN₄	详情	详情
(VII)	12263	Cyclopropylamine; Cyclopropanamine	765-30-0	C₃H₇N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

Alkylation of 4-hydroxy-3,5-dimethoxybenzaldehyde (VII) with 4-isopropylbenzyl chloride (VIII) affords the benzyloxy benzaldehyde (IX). Then, condensation of aldehyde (IX) with hydrazide (VI) furnishes the target N-acyl hydrazone

参考文献中间体

合成目标

【1】 Ling, A.; Plewe, M.; Gonzalez, J.; et al.; Human glucagon receptor antagonists based on alkylidene hydrazides. Bioorg Med Chem Lett 2002, 12, 4, 663.
【2】 Gonzales, J.; Sams, C.; Teng, M. (Alanex Corp.; Novo Nordisk A/S); Glucagon antagonists/inverse agonists. EP 0994848; WO 9901423 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	60848	3-cyano-4-hydroxybenzohydrazide		C₈H₇N₃O₂	详情	详情
(VII)	49243	3,5-Dimethoxy-4-hydroxybenzaldehyde; 4-Hydroxy-3,5-dimethoxybenzaldehyde; Syringaldehyde	134-96-3	C₉H₁₀O₄	详情	详情
(VIII)	33769	1-(chloromethyl)-4-isopropylbenzene	2051-18-5	C₁₀H₁₃Cl	详情	详情
(IX)	60849	4-[(4-isopropylbenzyl)oxy]-3,5-dimethoxybenzaldehyde		C₁₉H₂₂O₄	详情	详情

Extended Information