1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one -Drug Synthesis Database

【结构式】

【分子编号】18116

【品名】1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one

【CA登记号】1021-25-6

【分子式】C₁₃H₁₇N₃O

【分子量】231.2976

【元素组成】C 67.51% H 7.41% N 18.17% O 6.92%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(IV)

Alkylation of phenothiazine (I) with 1-bromo-3-chloropropane (II) in the presence of NaH in DMF at room temperature afforded chloropropyl compound (III), and then reaction of this compound with 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (IV) and K2CO3 in refluxing dioxan yielded the title compound.

参考文献中间体

合成目标

【1】 Bright, C.; Brown, T.J.; Cox, P.; Halley, F.; Lockey, P.; McLay,, I.M.; Moore, U.; Porter, B.; Williams, R.J.; Identification of a non peptidic RANTES antagonist. Bioorg Med Chem Lett 1998, 8, 7, 771-774.

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)	18114	N,N-dimethyl-10H-phenothiazine-2-sulfonamide	1090-78-4	C₁₄H₁₄N₂O₂S₂	详情	详情
(II)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(III)	18115	10-(3-chloropropyl)-N,N-dimethyl-10H-phenothiazine-2-sulfonamide		C₁₇H₁₉ClN₂O₂S₂	详情	详情
(IV)	18116	1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one	1021-25-6	C₁₃H₁₇N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The nitrosation of hexahydrophenalenone oxime (I) by means of NaNO2 and H2SO4 produced the N-nitroimine (II). Condensation of this intermediate with 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (III) in acetonitrile in the presence of molecular sieves gave rise to enamine (IV), which was finally reduced to the title amine using NaBH3CN.

参考文献中间体

合成目标

【1】 Adam, G.; Monsma, F.; Wichmann, J.; Jenck, F.; Galley, G.; Cesura, A.; Rover, S. (F. Hoffmann-La Roche AG); 8-Substd.-1,3,8-triazaspiro[4.5]decan-4-on derivs.. EP 0856514; US 6071925 .

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)	39762	2,3,3a,4,5,6-hexahydro-1H-phenalen-1-one oxime		C₁₃H₁₅NO	详情	详情
(II)	39763			C₁₃H₁₄N₂O₂	详情	详情
(III)	18116	1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one	1021-25-6	C₁₃H₁₇N₃O	详情	详情
(IV)	39764	8-(7,8,9,9a-tetrahydro-1H-phenalen-3-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one		C₂₆H₂₉N₃O	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VII)

Solution synthesis: In this case the target product is obtained by alkylation of 1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (VII) with 1-(chloromethyl)naphthalene (VIII) by means of K2CO3 and NaI in refluxing 2-butanone, followed by acylation with methyl bromoacetate (X) in DMF by means of NaH.

参考文献中间体

合成目标

【1】 Watson, B.; Thomsen, C.; Hohlweg, R. (Novo Nordisk A/S); Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes. EP 1080091; WO 9959997 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	18116	1-Phenyl-1,3,8-triazaspiro[4.5]decan-4-one	1021-25-6	C₁₃H₁₇N₃O	详情	详情
(VIII)	27408	1-(Chloromethyl)naphthalene	86-52-2	C₁₁H₉Cl	详情	详情
(IX)	47326	8-(1-naphthylmethyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one		C₂₄H₂₅N₃O	详情	详情
(X)	12309	methyl 2-bromoacetate; methyl bromoacetate	96-32-2	C₃H₅BrO₂	详情	详情

Extended Information