5-chloro-2-pentanone -Drug Synthesis Database

【结构式】

【分子编号】60460

【品名】5-chloro-2-pentanone

【CA登记号】

【分子式】C₅H₉ClO

【分子量】120.57856

【元素组成】C 49.81% H 7.52% Cl 29.4% O 13.27%

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：(VI)

Acylation of 4-nitroaniline (I) with 4-fluorobenzoyl chloride (II) affords benzanilide (III). Catalytic hydrogenation of the nitro group of (III) employing Pt/C then gives amine (IV). Diazotization of (IV), followed by reduction with SnCl2 leads to hydrazine (V). Reaction of 5-chloro-2-pentanone (VI) with dimethylamine yields the amino ketone (VII). Finally, the title compound is obtained by Fisher indole synthesis from aryl hydrazine (V) and ketone (VII) under acidic conditions.

参考文献中间体

合成目标

【1】 Xu, Y.-C.; Johnson, K.W.; Phebus, L.A.; et al.; N-[3-(2-Dimethylaminoethyl)-2-methyl-1-H-indol-5-yl]-4-fluorobenzamide: A potent, selective, and orally active 5-HT1F receptor agonist potentially useful for migraine therapy. J Med Chem 2001, 44, 24, 4031.
【2】 Johnson, K.W.; Phebus, L.A. (Eli Lilly and Company); Use of a serotonin 5-HT1F agonist in the manufacture of a medicament for treating or ameliorating the symptoms of common cold or allergic rhinitis. EP 0824917; US 5962473; WO 9806402 .
【3】 Fritz, J.E.; Hahn, P.J.; Kaldor, S.W.; Siegel, M.G.; Xu, Y.-C. (Eli Lilly and Company); N-[2-Substd.-3-(2-aminoethyl)-1H-indol-5-yl]-amides: New 5-HT1F agonists. EP 0768301; JP 1999513666; WO 9713512 .

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)	15547	4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline	100-01-6	C₆H₆N₂O₂	详情	详情
(II)	17263	4-fluorobenzoyl chloride	403-43-0	C₇H₄ClFO	详情	详情
(III)	60456	4-fluoro-N-(4-nitrophenyl)benzamide		C₁₃H₉FN₂O₃	详情	详情
(IV)	60457	N-(4-aminophenyl)-4-fluorobenzamide		C₁₃H₁₁FN₂O	详情	详情
(V)	60458	4-fluoro-N-(4-hydrazinophenyl)benzamide		C₁₃H₁₂FN₃O	详情	详情
(VI)	60460	5-chloro-2-pentanone		C₅H₉ClO	详情	详情
(VII)	60459	5-(dimethylamino)-2-pentanone		C₇H₁₅NO	详情	详情

Extended Information