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BILS-179 BS

Chemical Name: N-[N-[4-(2-Aminothiazol-4-yl)phenyl]carbamoylmethyl]-N-[1(S)-phenylethyl]pyridine-4-carboxamide
CAS No. 193346-73-5
项目整合开发状态: Preclinical
项目研究机构: Boehringer Ingelheim (Originator)
合成路线:The N-alkylation of N-(tert-butoxycarbonyl)glycine (I) with benzyl bromide (II) by means of NaH in THF gives N-benzyl-N-(tert-butoxycarbonyl)glycine (III),which is condensed with 4-aminoacetophenone (IV) by means of isobutyl chloroformate and TEA in dichloromethane yielding the corresponding glycinamide (V).The cyclization of (V) with thiourea (VI) by means of I2 in refluxing isopropanol affords,after work up,the N-benzyl-glycinamide (VII),which is finally acylated with pyridine-4-carbonyl chloride by means of TEA and DMAP in dichloromethane.

合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with (S)-alpha-methylbenzylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with 4-pyridylcarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 179 BS.

合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with 4-pyridylmethylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with cyclohexanecarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 103 BS.
📌 参考资料/链接：
参考文献标题:Phenyl thiazole derivs.with anti-herpes virus properties
文献作者:Hargrave,K.D.; Simoneau,B.; Faucher,A.-M.; Thavonekham,B.; Grygon,C.A.; Crute,J.J.(Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.)
参考来源:EP 0871619; JP 2000502702; US 6057451; WO 9724343

📄 详细内容


合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with (S)-alpha-methylbenzylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with 4-pyridylcarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 179 BS.

合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with 4-pyridylmethylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with cyclohexanecarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 103 BS.

参考文献标题:Antiherpes virus cpds.and methods for their preparation and use
文献作者:Hargrave,K.D.; Simoneau,B.; Faucher,A.-M.; Crute,J.J.; Thavonekham,B.; Grygon,C.(Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.)
参考来源:US 6288091


合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with (S)-alpha-methylbenzylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with 4-pyridylcarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 179 BS.

合成路线:The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III),which is then condensed with 4-pyridylmethylamine (IV) to yield the glycinamide derivative (V).The acylation of (V) with cyclohexanecarbonyl chloride affords the protected precursor (VI),which is finally deprotected to provide the target BILS 103 BS.
参考文献标题:Herpes simplex virus helicase-primase inhibitors are active in animal models of human disease
文献作者:Crute,J.J.; Grygon,C.A.; Hargrave,K.D.; Simoneau,B.; Faucher,A.M.; Bolger,G.; Kibler,P.; Liuzzi,M.; Cordingley,M.G.
参考来源:Nat Med 2002,8(4),386


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