-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】N2-[4-[5-(Acetamidomethyl)furan-2-yl]thiazol-2-yl]-N1-(2-ethoxybenzyl)guanidine

【CA登记号】168970-48-7 (tautomer)

【分子式】C₂₀H₂₃N₅O₃S

【分子量】413.50201

【开发单位】Fujisawa (Originator)

【药理作用】Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS

合成路线1 合成路线2

合成路线1

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.

参考文献中间体

【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2

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.

参考文献中间体

【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

Extended Information