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【结 构 式】

【分子编号】28318

【品名】2-(4-methylphenethyl)thiophene

【CA登记号】

【 分 子 式 】C13H14S

【 分 子 量 】202.32016

【元素组成】C 77.18% H 6.97% S 15.85%

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:(V)

The reaction of 2-(4-methylphenyl)acetic acid (I) with SOCl2 gives the corresponding acyl chloride (II), which is condensed with thiophene (III) by means SnCl4 yielding 2-(4-methylphenyl)-1-(2-thienyl)ethanone (IV). The reduction of (IV) with hydrazine and KOH in hot triethylene glycol affords 2-[2-(4-methylphenyl)ethyl]thiophene (V), which is condensed with 3,3-dimethylglutaric anhydride (VI), by means of AlCl3 in hot nitrobenzene giving the 5-oxopentanoic acid derivative (VII). The reduction of (VII) with hydrazine and KOH as before yields the pentanoic acid derivative (VIII), which is condensed with 4-(2,3,4-trimethoxybenzyl)piperazine (IX) by means of oxalyl chloride to afford the acyl piperazine (X). Finally, the amide group of (X) is reduced with LiAlH4 in ethyl ether.

1 Wierzbicki, M.; et al.; Amino derivatives of phenyl alkyl thiophene as inhibitors of bone resorption. Structure-activity relationship. Arzneim-Forsch Drug Res 1998, 48, 8, 840.
2 Wierzbicki, M.; Sauveur, F.; Bonnet, J.; Brisset, M.; Tordjman, C. (ADIR et Cie.); Thiophene derivs., process for their preparation and pharmaceutical compsns. containing them. AU 9166901; EP 0429370; FR 2655043; JP 1991190872; US 5061704 .
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) 28316 2-(4-methylphenyl)acetic acid 622-47-9 C9H10O2 详情 详情
(II) 21017 2-(4-methylphenyl)acetyl chloride 35675-44-6 C9H9ClO 详情 详情
(III) 13297 Thiophene 110-02-1 C4H4S 详情 详情
(IV) 28317 2-(4-methylphenyl)-1-(2-thienyl)-1-ethanone C13H12OS 详情 详情
(V) 28318 2-(4-methylphenethyl)thiophene C13H14S 详情 详情
(VI) 25549 4,4-dimethyldihydro-2H-pyran-2,6(3H)-dione 4160-82-1 C7H10O3 详情 详情
(VII) 28319 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]-5-oxopentanoic acid C20H24O3S 详情 详情
(VIII) 28320 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]pentanoic acid C20H26O2S 详情 详情
(IX) 24354 2,3-dimethoxy-4-(1-piperazinylmethyl)phenyl methyl ether C14H22N2O3 详情 详情
(X) 28321 3,3-dimethyl-5-[5-(4-methylphenethyl)-2-thienyl]-1-[4-(2,3,4-trimethoxybenzyl)-1-piperazinyl]-1-pentanone C34H46N2O4S 详情 详情
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