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

【结 构 式】

【分子编号】64345

【品名】N-(3,4-dimethyl-5-isoxazolyl)-4'-formyl-N-[(2-methoxyethoxy)methyl]-2'-methyl[1,1'-biphenyl]-2-sulfonamide

【CA登记号】

【 分 子 式 】C23H26N2O6S

【 分 子 量 】458.53532

【元素组成】C 60.25% H 5.72% N 6.11% O 20.94% S 6.99%

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:(VII)

Coupling of 2-bromobenzenesulfonyl chloride (I) with 5-amino-3,4-dimethylisoxazole (II) affords sulfonamide (III), which is further protected as the N-methoxyethoxymethyl derivative (IV) employing MEM-chloride in DMF. Lithiation of bromosulfonamide (IV), followed by treatment with trimethyl borate and acidic work up leads to the boronic acid intermediate (V). This is then subjected to Suzuki coupling with 4-bromo-3-methylbenzaldehyde (VI) to yield the biphenyl adduct (VII). After reduction of aldehyde (VII) to the benzylic alcohol (VIII) with NaBH4, reaction with methanesulfonyl chloride and diisopropylethylamine gives rise to the mesylate (IX) (1-3).

1 Tellew, J.E.; Baska, R.A.F.; Beyer, S.M.; Carlson, K.E.; Cornelius, L.A.; Fadnis, L.; Gu, Z..; Kunst, B.L.; Kowala, M.C.; Monshizadegan, H.; Murugesan, N.; Ryan, C.S.; Valentine, M.T.; Yang, Y.; Macor, J.E.; Discovery of 4'-[(Imidazol-1-yl)methyl]biphenyl-2-sulfonamides as dual endothelin/Angiotensin II receptor antagonists. Bioorg Med Chem Lett 2003, 13, 6, 1093.
2 Macor, J.E.; Murugesan, N.; Gu, Z.; Tellew, J.E. (Bristol-Myers Squibb Co.); Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists. EP 1094816; JP 2002519380; US 2002143024; WO 0001389 .
3 Macor, J.E.; Murugesan, N.; Gu, Z.; Tellew, J.E. (Bristol-Myers Squibb Co.); Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists. EP 1237888; WO 0144239 .
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) 26890 2-bromobenzenesulfonyl chloride 2905-25-1 C6H4BrClO2S 详情 详情
(II) 26891 3,4-dimethyl-5-isoxazolamine 19947-75-2 C5H8N2O 详情 详情
(III) 26892 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide C11H11BrN2O3S 详情 详情
(IV) 26893 2-bromo-N-(3,4-dimethyl-5-isoxazolyl)-N-[(2-methoxyethoxy)methyl]benzenesulfonamide C15H19BrN2O5S 详情 详情
(V) 60918 2-({(3,4-dimethyl-5-isoxazolyl)[(2-methoxyethoxy)methyl]amino}sulfonyl)phenylboronic acid C15H21BN2O7S 详情 详情
(VI) 64344 4-bromo-3-methylbenzaldehyde C8H7BrO 详情 详情
(VII) 64345 N-(3,4-dimethyl-5-isoxazolyl)-4'-formyl-N-[(2-methoxyethoxy)methyl]-2'-methyl[1,1'-biphenyl]-2-sulfonamide C23H26N2O6S 详情 详情
(VIII) 64346 N-(3,4-dimethyl-5-isoxazolyl)-4'-(hydroxymethyl)-N-[(2-methoxyethoxy)methyl]-2'-methyl[1,1'-biphenyl]-2-sulfonamide C23H28N2O6S 详情 详情
(IX) 64347 [2'-({(3,4-dimethyl-5-isoxazolyl)[(2-methoxyethoxy)methyl]amino}sulfonyl)-2-methyl[1,1'-biphenyl]-4-yl]methyl methanesulfonate C24H30N2O8S2 详情 详情
Extended Information