• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】5-tert-Butyl-3-(2,3-dichlorophenylureido)-1H-pyrrole-2-carboxylic acid methyl ester

【CA登记号】216573-65-8

【 分 子 式 】C17H19Cl2N3O3

【 分 子 量 】384.26528

【开发单位】Bayer (Originator)

【药理作用】Antiarthritic Drugs, Bone Diseases, Treatment of, METABOLIC DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Treatment of Osteoporosis, IL-6 Production Inhibitors, p38 Protein Kinase Inhibitors

合成路线1

Esterification of pyrrole-2-carboxylic acid (I) by treatment with TMSCl in MeOH yields methyl carboxylate (II), which is then condensed with tert-butyl chloride (III) by means of AlCl3 in 1,2-dichloroethane to provide methyl 5-tert-butyl pyrrole-2-carboxylate (IV). Nitration of pyrrolic derivative (IV) by reaction with HNO3/H2SO4 affords a mixture of compounds from which 3-nitropyrrole derivative (V) is cromatographically separated. Hydrogenation of (V) over Pd/C in MeOH allows conversion of the nitro group into an amino group to furnish methyl 3-amino-5-tert-butylpyrrole-2-carboxylate (VI), which is finally coupled to 2,3-dichlorophenyl isocyanate (VII) in dichloromethane to afford the desired compound.

1 Johnson, J.S.; Dally, R.; Redman, A.M.; et al.; p38 Kinase inhibitors for the treatment of arthritis and osteoporosis: Thienyl, furyl, and pyrrolyl ureas. Bioorg Med Chem Lett 2001, 11, 1, 9.
2 Gunn, D.; Ranges, G.; Chen, J.; Bombara, M.; Scott, W.; Rauner, D.; Redman, A.; Paulsen, H.; Smith, R.; Renick, J. (Bayer Corp.); Inhibition of p38 kinase activity by aryl ureas. WO 9852558 .
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) 31796 Pyrrole-2-carboxylic acid; 1H-pyrrole-2-carboxylic acid 634-97-9 C5H5NO2 详情 详情
(II) 45616 methyl 1H-pyrrole-2-carboxylate C6H7NO2 详情 详情
(III) 47128 2-chloro-2-methylpropane 507-20-0 C4H9Cl 详情 详情
(IV) 47129 methyl 5-(tert-butyl)-1H-pyrrole-2-carboxylate C10H15NO2 详情 详情
(V) 47130 methyl 5-(tert-butyl)-3-nitro-1H-pyrrole-2-carboxylate C10H14N2O4 详情 详情
(VI) 47131 methyl 3-amino-5-(tert-butyl)-1H-pyrrole-2-carboxylate C10H16N2O2 详情 详情
(VII) 29667 N-(2-chloroethyl)-N-[2-(3-methoxyphenyl)-1-methylethyl]-N-methylamine; N-(2-chloroethyl)-1-(3-methoxyphenyl)-N-methyl-2-propanamine C13H20ClNO 详情 详情
Extended Information