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【结 构 式】

【分子编号】34673

【品名】3-(2-methyl-1,3-dioxolan-2-yl)benzylamine; [3-(2-methyl-1,3-dioxolan-2-yl)phenyl]methanamine

【CA登记号】

【 分 子 式 】C11H15NO2

【 分 子 量 】193.24564

【元素组成】C 68.37% H 7.82% N 7.25% O 16.56%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

3-Acetylbenzonitrile (I) was protected as the ethylene ketal (II) employing ethylene glycol and boron trifluoride etherate. Reduction of the cyano group of (II) with LiAlH4 gave amine (III), and further ketal hydrolysis provided 3-acetylbenzylamine (IV). This was acetylated using acetyl chloride and Et3N to yield the intermediate amide (V). Alternatively, intermediate (V) was obtained by addition of methylmagnesium bromide to N-(3-cyanobenzyl)acetamide (VI). Bromination of (V) in dioxan furnished the bromoacetophenone (VII). This was cyclized to the aminothiazole (IX) by treatment with thiourea (VIII) in refluxing ethanol. Condensation of (IX) with benzoyl isothiocyanate (X) provided the benzoyl thiourea (XI). After selective hydrolysis of the benzoyl group of (XI) with NaOH in MeOH-H2O at 60 C, the resulting thiourea (XII) was methylated with iodomethane yielding S-methylisothiourea (XIII). Finally, displacement of the methylthio group with 2-methoxyetylamine (XIV) furnished the title guanidinothiazole.

1 Katsura, Y.; Tomishi, T.; Inoue, Y.; Takasugi, H. (Fujisawa Pharmaceutical Co., Ltd.); Guanidino thiazoles and their use as H2-receptor antagonist. EP 0545376; JP 1994321921; US 5532258 .
2 Inoue, Y.; Morinaga, C.; Ishikawa, H.; Takasugi, H.; Tomishi, T.; Matsumoto, Y.; Katsura, Y.; Sakane, K.; Anti-Helicobacter pylori agents.4. 2-(Substituted guanidino)-4-phenylthiazoles and some structurally rigid derivatives. J Med Chem 2000, 43, 17, 3315.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
19273 acetyl chloride 75-36-5 C2H3ClO 详情 详情
33623 bromo(methyl)magnesium 75-16-1 CH3BrMg 详情 详情
(I) 17992 m-Cyanoacetophenone; 3-acetylbenzonitrile 6136-68-1 C9H7NO 详情 详情
(II) 34665 3-(2-methyl-1,3-dioxolan-2-yl)benzonitrile C11H11NO2 详情 详情
(III) 34673 3-(2-methyl-1,3-dioxolan-2-yl)benzylamine; [3-(2-methyl-1,3-dioxolan-2-yl)phenyl]methanamine C11H15NO2 详情 详情
(IV) 34666 1-[3-(aminomethyl)phenyl]-1-ethanone C9H11NO 详情 详情
(V) 34674 N-(3-acetylbenzyl)acetamide C11H13NO2 详情 详情
(VI) 34667 N-(3-cyanobenzyl)acetamide C10H10N2O 详情 详情
(VII) 34668 N-[3-(2-bromoacetyl)benzyl]acetamide C11H12BrNO2 详情 详情
(VIII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(IX) 34669 N-[3-(2-amino-1,3-thiazol-4-yl)benzyl]acetamide C12H13N3OS 详情 详情
(X) 23530 benzoyl isothiocyanate 532-55-8 C8H5NOS 详情 详情
(XI) 34670 N-[3-(2-[[(benzoylamino)carbothioyl]amino]-1,3-thiazol-4-yl)benzyl]acetamide C20H18N4O2S2 详情 详情
(XII) 34671 N-(3-[2-[(aminocarbothioyl)amino]-1,3-thiazol-4-yl]benzyl)acetamide C13H14N4OS2 详情 详情
(XIII) 34672 4-[3-[(acetamido)methyl]phenyl]-2-[[(E)-amino(methylsulfanyl)methylidene]amino]-1,3-thiazole C14H16N4OS2 详情 详情
(XIV) 34675 2-methoxyethylamine; 2-methoxy-1-ethanamine 109-85-3 C3H9NO 详情 详情
Extended Information