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【结 构 式】

【分子编号】51871

【品名】methyl 5-[[4-(acetamido)phenyl]sulfanyl]-1H-benzimidazol-2-ylcarbamate

【CA登记号】

【 分 子 式 】C17H16N4O3S

【 分 子 量 】356.4052

【元素组成】C 57.29% H 4.52% N 15.72% O 13.47% S 9%

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:(VI)

The condensation between 4-(acetylamino)thiophenol (I) and 5-chloro-2-nitroaniline (II) produced the diaryl sulfide (III). Nitro group reduction in (III) employing SnCl2 gave the phenylenediamine (IV), which was cyclized to the benzimidazole (VI) upon treatment with N,N'-bis(methoxycarbonyl)-S-methylisothiourea (V). Hydrolysis of the acetamido group of (VI) with HCl in MeOH afforded aniline (VII). This was acylated with N-Boc-alanine (VIII) in the presence of EDC to yield amide (IX). The N-Boc protecting group of (IX) was finally removed by treatment with trifluoroacetic acid.

1 Lewis, G.S.; Nolan, J.; Davis, P.D.; Naylor, M.A.; Thomson, P.; Hill, S.A.; Benzimidazole carbamates: A new structural class of vascular targeting agents. Proc Amer Assoc Cancer Res 2001, 42, Abst 2000.
2 Davis, P.D. (Angiogene Pharmaceuticals Ltd.); Benzimidazole vascular damaging agents. EP 1140078; WO 0041669 .
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) 34329 N-(4-sulfanylphenyl)acetamide 1126-81-4 C8H9NOS 详情 详情
(II) 15709 5-chloro-2-nitrophenylamine; 5-chloro-2-nitroaniline 1635-61-6 C6H5ClN2O2 详情 详情
(III) 51869 N-[4-[(3-amino-4-nitrophenyl)sulfanyl]phenyl]acetamide C14H13N3O3S 详情 详情
(IV) 51870 N-[4-[(3,4-diaminophenyl)sulfanyl]phenyl]acetamide C14H15N3OS 详情 详情
(V) 28696 methyl (Z)-[(methoxycarbonyl)amino](methylsulfanyl)methylidenecarbamate C6H10N2O4S 详情 详情
(VI) 51871 methyl 5-[[4-(acetamido)phenyl]sulfanyl]-1H-benzimidazol-2-ylcarbamate C17H16N4O3S 详情 详情
(VII) 51872 methyl 5-[(4-aminophenyl)sulfanyl]-1H-benzimidazol-2-ylcarbamate C15H14N4O2S 详情 详情
(VIII) 26450 Boc-L-Alanine;(S)-2-((tert-butoxycarbonyl)amino)propanoic acid;N-Boc-L-alanine; (2S)-2-[(tert-butoxycarbonyl)amino]propionic acid 15761-38-3 C8H15NO4 详情 详情
(IX) 51873 methyl 5-[[4-([(2S)-2-[(tert-butoxycarbonyl)amino]propanoyl]amino)phenyl]sulfanyl]-1H-benzimidazol-2-ylcarbamate C23H27N5O5S 详情 详情
Extended Information