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【结 构 式】 
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【分子编号】19167 【品名】3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine 【CA登记号】1477-55-0 |
【 分 子 式 】C8H12N2 【 分 子 量 】136.19676 【元素组成】C 70.55% H 8.88% N 20.57% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of m-xylenediamine (I) with triethylamine and di-tert-butyldicarbonate (II) gives the corresponding tert-butyl N-[3-(aminomethyl)benzyl] carbamate hydrochloride (III), which is converted into the tert-butyl N-[3-((acetimidoyl)aminomethyl]benzyl) carbamate hydrochloride (VII) by reaction with S-benzylthioacetimidate hydrochloride (VI). This intermediate (VI) could be obtained by reaction of thioacetamide (IV) with benzyl chloride (V). Finally, compound (VII) is deprotected with HCl to afford the corresponding N-[3-(aminomethyl)benzyl] acetamidine hydrochloride.
| 【1】 Itabashi, K.; Takido, T.; An efficient synthesis of unsymmetrical sulfides using liquid-liquid phase transfer catalysis. Synthesis 1987, 817. |
| 【2】 Oplinger, J.A.; Garvey, E.P.; Furfine, E.S.; Shearer, B.G.; Collins, J.L. (Glaxo Wellcome plc); Acetamidine derivs. and their use as inhibitors for the nitric oxide synthase. EP 0799191; JP 1999500711; US 5866612; WO 9619440 . |
| 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) | 19167 | 3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine | 1477-55-0 | C8H12N2 | 详情 | 详情 |
| (II) | 13214 | Di-tert-butyldicarbonate; Dicarbonic acid bis(1,1-dimethylethyl) ester; dicarbonic acid di-tert-butyl ester pyrocarbonic acid di-tert-butyl ester; bis(1,1-dimethylethyl) dicarbonate di-tert-butyl pyrocarbonate | 24424-99-5 | C10H18O5 | 详情 | 详情 |
| (III) | 19169 | tert-butyl N-[3-(aminomethyl)benzyl]carbamate; tert-butyl 3-(aminomethyl)benzylcarbamate | 108467-99-8 | C13H20N2O2 | 详情 | 详情 |
| (IV) | 19170 | ethanethioamide | 62-55-5 | C2H5NS | 详情 | 详情 |
| (V) | 19171 | 1-(Chloromethyl)benzene; Benzyl chloride | 100-44-7 | C7H7Cl | 详情 | 详情 |
| (VI) | 19172 | benzyl ethanimidothioate | C9H11NS | 详情 | 详情 | |
| (VII) | 19173 | tert-butyl 3-[(ethanimidoylamino)methyl]benzylcarbamate | C15H23N3O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The reaction of m-xylene-alpha,alpha'-diamine (I) with N,N'-bis(tert-butoxycarbonyl)pyrazole-1-carboxamidine (II) in THF gives the protected guanidine (III), which is acylated at the free amino group with 2,3-diphenylpropionyl chloride (IV) and triethylamine in dichloromethane affording the amide (V). The condensation of (V) with tetrahydrofuran-2-ylmethylamine (VI) in refluxing THF affords the protected amidinourea (VII), which is finally treated with TFA in dichloromethane.
| 【1】 Biftu, T.; et al.; Synthesis and SAR of oxodiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 138. |
| 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) | 19167 | 3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine | 1477-55-0 | C8H12N2 | 详情 | 详情 |
| (II) | 29482 | N,N-bis-Boc-1-guanylpyrazole; tert-butyl (E)-[(tert-butoxycarbonyl)amino](1H-pyrazol-1-yl)methylidenecarbamate | 152120-54-2 | C14H22N4O4 | 详情 | 详情 |
| (III) | 29483 | tert-butyl (Z)-[[3-(aminomethyl)benzyl]amino][(tert-butoxycarbonyl)amino]methylidenecarbamate | C19H30N4O4 | 详情 | 详情 | |
| (IV) | 29484 | 2,3-diphenylpropanoyl chloride | C15H13ClO | 详情 | 详情 | |
| (V) | 29485 | tert-butyl (Z)-[(tert-butoxycarbonyl)amino][(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]methylidenecarbamate | C34H42N4O5 | 详情 | 详情 | |
| (VI) | 27335 | Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine | 4795-29-3 | C5H11NO | 详情 | 详情 |
| (VII) | 29486 | tert-butyl (Z)-[(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]([[(tetrahydro-2-furanylmethyl)amino]carbonyl]amino)methylidenecarbamate | C35H43N5O5 | 详情 | 详情 |