(1S,2S)-2-aminocyclohexylamine; (1S,2S)-1,2-cyclohexanediamine -Drug Synthesis Database

【结构式】

【分子编号】23788

【品名】(1S,2S)-2-aminocyclohexylamine; (1S,2S)-1,2-cyclohexanediamine

【CA登记号】21436-03-3

【分子式】C₆H₁₄N₂

【分子量】114.19064

【元素组成】C 63.11% H 12.36% N 24.53%

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：(I)

Reductive alkylation of trans-1,2-cyclohexanediamine (I) with veratraldehyde (II) in the presence of NaBH4 afforded the corresponding bis-(benzylamino)cyclohexane derivative (III). This was then alkylated with solanesyl bromide (IV) in THF to furnish the title compound

参考文献中间体

合成目标

【1】 Inomata, K.; Takahashi, T.; Inoue, H.; Taniuchi, M.; Yamazaki, H.; Suzuki, M.; Takazawa, T.; Kawamura, K.; Oshida, N.; Ikemoto, H.; Kishie, T. (Nisshin Seifun Group Inc.); Isoprene derivs.. EP 0787716; JP 1997268162 .

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)	23788	(1S,2S)-2-aminocyclohexylamine; (1S,2S)-1,2-cyclohexanediamine	21436-03-3	C₆H₁₄N₂	详情	详情
(II)	18304	3,4-Dimethoxybenzaldehyde; Veratraldehyde	120-14-9	C₉H₁₀O₃	详情	详情
(III)	60503	(1R,2R)-N~1~,N~2~-bis(3,4-dimethoxybenzyl)-1,2-cyclohexanediamine; N-(3,4-dimethoxybenzyl)-N-{(1R,2R)-2-[(3,4-dimethoxybenzyl)amino]cyclohexyl}amine		C₂₄H₃₄N₂O₄	详情	详情
(IV)	60504	(2E,6E,10E,14E,18E,22E,26E,30E)-1-bromo-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene		C₄₅H₇₃Br	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

Treatment of 7-oxo-7H-benzo[e]perimidine-4-carboxylic acid (I) with carbonyldiimidazole produced the corresponding acyl imidazolide (II). Reaction of this intermediate with 1,2-cyclohexanediamine (III) in DMF at 50 C afforded a mixture of amide (IV) and the title hexacyclic compound (V), which were separated by means of preparative HPLC. Alternatively, imidazolide (II) was first coupled with one equivalent of diamine (III) in DMF at r.t. to give amide (IV), which was then converted into the title compound by treatment with an excess of diamine (III) at 50 C.

参考文献中间体

合成目标

【1】 Dhanoa, D.S.; Luthin, D.R.; May, J.M.; Rabinovich, A.K.; Youngblood, K.L.; Bhumralkar, D.R.; Bychowski, R.A.; Synthesis and biological activity of oxo-7H-benzo[. Bioorg Med Chem Lett 1999, 9, 5, 765.

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)	23786	7-oxo-7H-benzo[e]perimidine-4-carboxylic acid	65359-16-2	C₁₆H₈N₂O₃	详情	详情
(II)	23787	4-(1H-imidazol-1-ylcarbonyl)-7H-benzo[e]perimidin-7-one		C₁₉H₁₀N₄O₂	详情	详情
(III)	23788	(1S,2S)-2-aminocyclohexylamine; (1S,2S)-1,2-cyclohexanediamine	21436-03-3	C₆H₁₄N₂	详情	详情
(IV)	23789	N-[(1S,2S)-2-aminocyclohexyl]-7-oxo-7H-benzo[e]perimidine-4-carboxamide		C₂₂H₂₀N₄O₂	详情	详情
(V)	23790	(9aR,13aR)-N-[(1S,2S)-2-aminocyclohexyl]-15-oxo-9a,10,11,12,13,13a,14,15-octahydro-9H-benzo[7,8]quinazolino[5,4-ab]phenazine-8-carboxamide		C₂₈H₃₀N₆O₂	详情	详情

Extended Information