6-[(5-phenyl-1H-pyrazol-3-yl)oxy]-1-hexanol -Drug Synthesis Database

【结构式】

【分子编号】20515

【品名】6-[(5-phenyl-1H-pyrazol-3-yl)oxy]-1-hexanol

【CA登记号】

【分子式】C₁₅H₂₀N₂O₂

【分子量】260.33608

【元素组成】C 69.2% H 7.74% N 10.76% O 12.29%

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：(III)

Reaction of 6-chlorohexanol (I) with 3-phenyl-5-pyrazolone (II) in the presence of K2CO3 in DMF gives 6-(5-phenyl-3-pyrazolyloxy)hexyl alcohol (III), which affords the crystalline acetoacetate derivative (IV) by esterification of (III) with diketene in the presence of triethylamine. Reaction of (IV) and ammonium carbonate in refluxing methanol gives 3-aminocrotonic acid 6-(5-phenyl-3-pyrazolyloxy)hexyl ester (V). This compound is finally cyclized with methyl 3-nitrobenzylidene acetoacetate (VI) in ethanol.

参考文献中间体

合成目标

【1】 Masato, K.; Shinji, T.; Kozo, H.; Susumu, T. (Tokyo Tanabe Co., Ltd.); Novel 1,4-dihydropyridine derivatives. DE 3230400; FR 2511370; FR 8214008; GB 2108108; JP 88023193; US 4418197 .
【2】 Masato, K.; Shinji, T.; Tsutomu, A.; Setagaya, S.C.; Susumu, T. (Tokyo Tanabe Co., Ltd.); Powdery preparation of amorphous dihydropyridine compound. EP 0147171; JP 60139688 .
【3】 Kamibayashi, M.; CV-159. Drugs Fut 1989, 14, 3, 206.

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)	20513	6-chloro-1-hexanol	2009-83-8	C₆H₁₃ClO	详情	详情
(II)	20514	5-phenyl-2,4-dihydro-3H-pyrazol-3-one		C₉H₈N₂O	详情	详情
(III)	20515	6-[(5-phenyl-1H-pyrazol-3-yl)oxy]-1-hexanol		C₁₅H₂₀N₂O₂	详情	详情
(IV)	20516	6-[(5-phenyl-1H-pyrazol-3-yl)oxy]hexyl 3-amino-3-oxopropanoate		C₁₈H₂₃N₃O₄	详情	详情
(V)	20517	6-[(5-phenyl-1H-pyrazol-3-yl)oxy]hexyl (E)-3-amino-2-butenoate		C₁₉H₂₅N₃O₃	详情	详情
(VI)	12276	methyl (Z)-2-acetyl-3-(3-nitrophenyl)-2-propenoate		C₁₂H₁₁NO₅	详情	详情
(VII)	11367	4-Methylene-2-oxetanone; Acetyl ketene	674-82-8	C₄H₄O₂	详情	详情

Extended Information