【结 构 式】 |
【分子编号】63370 【品名】N-[3-(aminomethyl)phenyl]-2-thiophenecarboximidamide 【CA登记号】 |
【 分 子 式 】C12H13N3S 【 分 子 量 】231.32144 【元素组成】C 62.31% H 5.66% N 18.17% S 13.86% |
合成路线1
该中间体在本合成路线中的序号:(V)Reduction of N-Boc-3-nitrobenzylamine (I) by catalytic hydrogenation over Pd/C yields aniline (II). This is then condensed with S-methyl-2-thiophenethiocarboximide (III) to furnish amidine (IV). Subsequent acidic Boc group cleavage yields amine (V).
【1】 Auvin, S.; Auget, M.; Navet, E.; Harnett, J.J.; Viossat, I.; Schulz, J.; Bigg, D.; Chabrier, P.-E.; Novel inhibitors of neuronal nitric oxide synthase with potent antioxidant properties. Bioorg Med Chem Lett 2003, 13, 2, 209. |
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) | 63368 | 1,1-dimethylethyl (3-nitrophenyl)methylcarbamate | C12H16N2O4 | 详情 | 详情 | |
(II) | 39660 | tert-butyl 3-aminobenzylcarbamate | C12H18N2O2 | 详情 | 详情 | |
(III) | 34836 | methyl 2-thiophenecarbimidothioate | C6H7NS2 | 详情 | 详情 | |
(IV) | 63369 | 1,1-dimethylethyl (3-{[imino(2-thiophenyl)methyl]amino}phenyl)methylcarbamate | C17H21N3O2S | 详情 | 详情 | |
(V) | 63370 | N-[3-(aminomethyl)phenyl]-2-thiophenecarboximidamide | C12H13N3S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(V)3,5-Diisopropyl-4-hydroxybenzaldehyde (VI) is esterified with acetyl chloride, producing acetate (VII). Subsequent Wittig condensation of aldehyde (VII) with carboethoxymethylene triphenylphosphorane leads to the cinnamyl derivative (VIII), which is further hydrogenated to the arylpropionic ester (IX). After saponification of ester (IX) with LiOH, the resultant carboxylic acid (X) is coupled to amine (V), producing amide (XI). Finally, amide reduction with borane in THF gives rise to the target amine.
【1】 Auvin, S.; Auget, M.; Navet, E.; Harnett, J.J.; Viossat, I.; Schulz, J.; Bigg, D.; Chabrier, P.-E.; Novel inhibitors of neuronal nitric oxide synthase with potent antioxidant properties. Bioorg Med Chem Lett 2003, 13, 2, 209. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
14182 | ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane | 1099-45-2 | C22H21O2P | 详情 | 详情 | |
(V) | 63370 | N-[3-(aminomethyl)phenyl]-2-thiophenecarboximidamide | C12H13N3S | 详情 | 详情 | |
(VI) | 63371 | 4-hydroxy-3,5-bis(1-methylethyl)benzaldehyde | C13H18O2 | 详情 | 详情 | |
(VII) | 63372 | 4-formyl-2,6-bis(1-methylethyl)phenyl acetate | C15H20O3 | 详情 | 详情 | |
(VIII) | 63373 | ethyl 3-[4-(acetyloxy)-3,5-bis(1-methylethyl)phenyl]-2-propenoate | C19H26O4 | 详情 | 详情 | |
(IX) | 63374 | ethyl 3-[4-(acetyloxy)-3,5-bis(1-methylethyl)phenyl]propanoate | C19H28O4 | 详情 | 详情 | |
(X) | 63375 | 3-[4-hydroxy-3,5-bis(1-methylethyl)phenyl]propanoic acid | C15H22O3 | 详情 | 详情 | |
(XI) | 63376 | 3-[4-hydroxy-3,5-bis(1-methylethyl)phenyl]-N-[(3-{[imino(2-thiophenyl)methyl]amino}phenyl)methyl]propanamide | C27H33N3O2S | 详情 | 详情 |