【结 构 式】 |
【分子编号】38253 【品名】2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine 【CA登记号】 |
【 分 子 式 】C9H13NO 【 分 子 量 】151.20836 【元素组成】C 71.49% H 8.67% N 9.26% O 10.58% |
合成路线1
该中间体在本合成路线中的序号:(IV)Reaction of 4-methylphenol (I) with NaH in DMF and 3-fluorobenzaldehyde (II) yields aldehyde (III), which will be converted into secondary amine (V) via a reductive amination with amine (IV) in presence of NaBH3CN in MeOH and catalytic HOAc. Amine (V) couples with dianhydride (VI) in THF in presence of NMM or alternatively in toluene and Et3N. Final treatment with Na2CO3 in THF yields the desired product.
【1】 Sullivan, G.M.; Rosenberg, S.H.; Prasad, R.N.; O'Connor, S.J.; Donner, B.G.; Fakhoury, S.A.; Fung, K.L.; Stout, D.M.; Rockway, T.W.; Baker, W.R.; Shen, W.; Garvey, D.S. (Abbott Laboratories Inc.); Benzene, pyridine, naphthalene or benzophenone derivs. as inhibitors of squalene synthetase and protein farnesyltransferase. WO 9634851 . |
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) | 37678 | p-cresol | 106-44-5 | C7H8O | 详情 | 详情 |
(II) | 18887 | 3-Fluorobenzaldehyde | 456-48-4 | C7H5FO | 详情 | 详情 |
(III) | 41482 | 3-(4-methylphenoxy)benzaldehyde | 79124-75-7 | C14H12O2 | 详情 | 详情 |
(IV) | 38253 | 2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine | C9H13NO | 详情 | 详情 | |
(V) | 41483 | N-(2-ethoxybenzyl)[3-(4-methylphenoxy)phenyl]methanamine; N-(2-ethoxybenzyl)-N-[3-(4-methylphenoxy)benzyl]amine | n/a | C23H25NO2 | 详情 | 详情 |
(VI) | 41484 | 1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone | 89-32-7 | C10H2O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(VIII)The cyclization of N-[5-(2-chloroacetyl)furan-2-ylmethylacetamide (I) with thiourea (II) in ethanol gives the thiazole (III), which is condensed with benzoyl isothiocyanate (IV) in acetone to yield the benzoylthiourea (V). The hydrolysis of (V) with NaOH in aqueous methanol affords the thiourea (VI), which is treated with methyl iodide in methanol to give the S-methylisothiourea (VII). Finally, this compound is condensed with 2-ethoxybenzylamine (VIII) in EtOH/AcOH.
【1】 Matsumoto, Y.; Takasugi, H.; Ohno, M.; Sakane, K.; Ishikawa, H.; Nishino, S.; Morinaga, C.; Katsura, Y.; Anti-Helicobacter pylori Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles. J Med Chem 1999, 42, 15, 2920. |
【2】 Katsura, Y.; Ohno, M.; Nishino, S.; Tomishi, T.; Takasugi, H. (Fujisawa Pharmaceutical Co., Ltd.); Furylthiazoles and their use as H2-receptor antagonists and antimicrobials. JP 1997507222; WO 9518126 . |
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) | 38248 | N-[[5-(2-chloroacetyl)-2-furyl]methyl]acetamide | C9H10ClNO3 | 详情 | 详情 | |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 38249 | N-[[5-(2-amino-1,3-thiazol-4-yl)-2-furyl]methyl]acetamide | C10H11N3O2S | 详情 | 详情 | |
(IV) | 23530 | benzoyl isothiocyanate | 532-55-8 | C8H5NOS | 详情 | 详情 |
(V) | 38250 | N-[[5-(2-[[(benzoylamino)carbothioyl]amino]-1,3-thiazol-4-yl)-2-furyl]methyl]acetamide | C18H16N4O3S2 | 详情 | 详情 | |
(VI) | 38251 | N-[(5-[2-[(aminocarbothioyl)amino]-1,3-thiazol-4-yl]-2-furyl)methyl]acetamide | C11H12N4O2S2 | 详情 | 详情 | |
(VII) | 38252 | 4-[5-[(acetamido)methyl]-2-furyl]-2-[[(Z)-amino(methylsulfanyl)methylidene]amino]-1,3-thiazole | C12H14N4O2S2 | 详情 | 详情 | |
(VIII) | 38253 | 2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine | C9H13NO | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号:(VIII)The reaction of dithiobiuret (IX) with methyl iodide in ethanol gives the corresponding S-methyl derivative (X), which is condensed with 2-ethoxybenzylamine (VIII) in ethanol yielding the guanidine (XI). Finally, this compound is cyclized with N-[5-(2-chloroacetyl)furan-2-ylmethylacetamide (I) in ethanol.
【1】 Matsumoto, Y.; Takasugi, H.; Ohno, M.; Sakane, K.; Ishikawa, H.; Nishino, S.; Morinaga, C.; Katsura, Y.; Anti-Helicobacter pylori Agents. 3. 2-[(Arylalkyl)guanidino]-4-furylthiazoles. J Med Chem 1999, 42, 15, 2920. |
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) | 38248 | N-[[5-(2-chloroacetyl)-2-furyl]methyl]acetamide | C9H10ClNO3 | 详情 | 详情 | |
(VIII) | 38253 | 2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine | C9H13NO | 详情 | 详情 | |
(IX) | 38254 | amino[(aminocarbothioyl)amino]thioxomethane | 541-53-7 | C2H5N3S2 | 详情 | 详情 |
(X) | 38255 | N-[(Z)-amino(methylsulfanyl)methylidene]thiourea | C3H7N3S2 | 详情 | 详情 | |
(XI) | 38256 | N-[(E)-amino[(2-ethoxybenzyl)amino]methylidene]thiourea | C11H16N4OS | 详情 | 详情 |