2,2-dimethylcyclopentanecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】43359

【品名】2,2-dimethylcyclopentanecarbonitrile

【CA登记号】

【分子式】C₈H₁₃N

【分子量】123.19796

【元素组成】C 77.99% H 10.64% N 11.37%

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)

Treatment of 2,2-dimethylcyclopentanone (I) with tosylmethyl isocyanide and potassium tert-butoxide produced nitrile (II), which was reduced to amine (III) employing LiAlH4 in THF. Coupling of amine (III) with mono-methyl terephthalate (IV) by means of EDC and HOBt gave amide (V). The target oxadiazole system was then obtained by condensation of (V) with N-hydroxypentamidine (VI) in the presence of NaH, and the (S)-enantiomer was isolated by using chiral HPLC.

参考文献中间体

合成目标

【1】 Poss, M.A.; Lloyd, J.; Rovnyak, G.C.; Caulfield, T.J.; Atwal, K.S.; Stein, P.D.; Ahmad, S. (Bristol-Myers Squibb Co.); Benzoic acid derivs. and related cpds. as antiarrhythmic agents. WO 9837068 .

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)	43358	2,2-dimethylcyclopentanone		C₇H₁₂O	详情	详情
(II)	43359	2,2-dimethylcyclopentanecarbonitrile		C₈H₁₃N	详情	详情
(III)	43360	(2,2-dimethylcyclopentyl)methylamine; (2,2-dimethylcyclopentyl)methanamine		C₈H₁₇N	详情	详情
(IV)	43361	4-(methoxycarbonyl)benzoic acid	1679-64-7	C₉H₈O₄	详情	详情
(V)	43362	methyl 4-([[(2,2-dimethylcyclopentyl)methyl]amino]carbonyl)benzoate		C₁₇H₂₃NO₃	详情	详情
(VI)	43363	N'-hydroxypentanimidamide		C₅H₁₂N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Amine (III) was synthesized from 2,2-dimethylcyclopentanone (I) by treatment with tosylmethyl isocyanide, followed by reduction of the resultant nitrile (II) with LiAlH4. Condensation of 4-cyanobenzoic acid (IV) with amine (III) produced the corresponding amide (V). Subsequent addition of hydroxylamine to the cyano group of (V) gave rise to the hydroxyamidine (VI). The target oxadiazole derivative was then obtained by condensation of (VI) with 4,4,4-trifluorobutyric acid (VII), followed by cyclization under basic conditions. Separation of the enantiomers was carried out by chiral preparative HPLC.

参考文献中间体

合成目标

【1】 LLoyd, J.; et al.; Design and synthesis of 4-substituted benzamides as potent, selective, and orally bioavailable IKS blockers. J Med Chem 2001, 44, 23, 3764.
【2】 Poss, M.A.; Lloyd, J.; Rovnyak, G.C.; Caulfield, T.J.; Atwal, K.S.; Stein, P.D.; Ahmad, S. (Bristol-Myers Squibb Co.); Benzoic acid derivs. and related cpds. as antiarrhythmic agents. WO 9837068 .

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)	43358	2,2-dimethylcyclopentanone		C₇H₁₂O	详情	详情
(II)	43359	2,2-dimethylcyclopentanecarbonitrile		C₈H₁₃N	详情	详情
(III)	43360	(2,2-dimethylcyclopentyl)methylamine; (2,2-dimethylcyclopentyl)methanamine		C₈H₁₇N	详情	详情
(IV)	36897	4-cyanobenzoic acid；4-Carboxybenzonitrile;p-Carboxybenzonitrile	619-65-8	C₈H₅NO₂	详情	详情
(V)	52509	4-cyano-N-[(2,2-dimethylcyclopentyl)methyl]benzamide		C₁₆H₂₀N₂O	详情	详情
(VI)	52510	4-[amino(hydroxyimino)methyl]-N-[(2,2-dimethylcyclopentyl)methyl]benzamide		C₁₆H₂₃N₃O₂	详情	详情
(VII)	14781	4,4,4-Trifluorobutyric acid	406-93-9	C₄H₅F₃O₂	详情	详情

Extended Information