7-methyl-2-naphthonitrile -Drug Synthesis Database

【结构式】

【分子编号】24987

【品名】7-methyl-2-naphthonitrile

【CA登记号】

【分子式】C₁₂H₉N

【分子量】167.2102

【元素组成】C 86.2% H 5.43% N 8.38%

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：(IV)

The bromination of 2,7-dimethylnaphthalene (I) with N-bromosuccinimide (NBS) and UV light in CCl4 gives the monobromo derivative (II), which is treated with 2-nitropropane/NaOMe to yield 7-methylnaphthalene-2-carbaldehyde (III). The reaction of (III) with hydroxylamine-O-sulfonic acid affords the nitrile (IV), which is brominated with NBS as before to give 7-(bromomethyl)naphthalene-2-carbonitrile (V). The condensation of (V) with 2-[4-[1-(tert-butoxycarbonyl)pyrrolidin-3(S)-yloxy]phenyl]acetic acid ethyl ester (VI) by means of lithium bis(trimethylsilyl)amide yields 2-[4-[1-(tert-butoxycarbonyl)pyrrolidin-3(S)-yloxy]phenyl]-3-(7-cyano-2-naphthyl)propionic acid ethyl ester (VII) as a diastereomeric mixture. This mixture was worked up as already described to obtain the target compound DX-9065a.

参考文献中间体

合成目标

【1】 Engh, R.A.; Neidlein, R.; Bradstetter, H.; Strein, K.; Koczmierz, R.; Marzenell, K.; Leibert, H.; von der Saal, W.; Kehr, R.; A short synthesis of the factor-Xa inhibitor DX-9065 a using palladium-catalyzed key steps. Helv Chim Acta 1997, 80, 892.

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)	24984	2,7-dimethylnaphthalene	582-16-1	C₁₂H₁₂	详情	详情
(II)	24985	2-(bromomethyl)-7-methylnaphthalene		C₁₂H₁₁Br	详情	详情
(III)	24986	7-methyl-2-naphthaldehyde	52988-18-8	C₁₂H₁₀O	详情	详情
(IV)	24987	7-methyl-2-naphthonitrile		C₁₂H₉N	详情	详情
(V)	24988	7-(bromomethyl)-2-naphthonitrile		C₁₂H₈BrN	详情	详情
(VI)	24989	tert-butyl (3S)-3-[4-(2-ethoxy-2-oxoethyl)phenoxy]-1-pyrrolidinecarboxylate		C₁₉H₂₇NO₅	详情	详情
(VII)	16291	tert-butyl (3S)-3-(4-[1-[(7-cyano-2-naphthyl)methyl]-2-ethoxy-2-oxoethyl]phenoxy)-1-pyrrolidinecarboxylate		C₃₁H₃₂N₂O₅	详情	详情
(VIII)	24991	tert-butyl (3S)-3-(4-[(1S)-1-[(7-cyano-2-naphthyl)methyl]-2-ethoxy-2-oxoethyl]phenoxy)-1-pyrrolidinecarboxylate		C₃₁H₃₄N₂O₅	详情	详情

Extended Information