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

【结 构 式】

【分子编号】13522

【品名】N-(4-Oxo-6-phenoxy-3,4-dihydro-2H-chromen-7-yl)methanesulfonamide

【CA登记号】

【 分 子 式 】C16H15NO5S

【 分 子 量 】333.36484

【元素组成】C 57.65% H 4.54% N 4.2% O 24% S 9.62%

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 reduction of 3-nitro-4-phenoxyphenol (I) with Fe, aqueous HCl gives 3-amino-4-phenoxyphenol (II), which is acylated with methanesulfonyl chloride by means of pyridine in dichloromethane affording 3-(methylsulfonamido)-4-phenoxyphenol (III). The condensation of (III) with 3-chloropropionic acid (IV) by means of NaOH in water gives 3-[3-(methylsulfonamido)-4-phenoxyphenoxy]propionic acid (V), which is cyclized by means of polyphosphoric acid at 65-70 C yielding 7-(methylsulfonamido)-6-phenoxy-3,4-dihydro-2H-1-benzopyran-4-one (VI). The bromination of (VI) with Br2 in CHCl3 affords 3-bromo-7-(methylsulfonamido)-6-phenoxy-3,4-dihydro-2H-1-benzopyran-4-one (VII), which is treated with sodium azide in DMF at 70-75 C giving 3-amino-7-(methylsulfonamido)-6-phenoxy-2H-1-benzopyran-4-one (VIII). Finally, this compound is formylated with formic acid in acetic anhydride.

1 Takano, S.; Yoshida, C.; Inaba, T.; Tanaka, K.; Takeno, R.; Nagaki, H.; Shimotori, T.; Makino, S. (Toyama Chemical Co., Ltd.); 4H-Benzopyran-4-one derivs. and their salts, their processes of production and pharmaceutical compsns. containing them. AU 8823489; CH 679397; FR 2621585; GB 2210879; JP 1995267943; US 4954518 .
2 Mealy, N.; Prous, J.; Castaner, J.; T-614. Drugs Fut 1993, 18, 8, 714.
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) 13517 3-Nitro-4-phenoxyphenol C12H9NO4 详情 详情
(II) 13518 3-Amino-4-phenoxyphenol C12H11NO2 详情 详情
(III) 13519 N-(5-Hydroxy-2-phenoxyphenyl)methanesulfonamide C13H13NO4S 详情 详情
(IV) 13520 3-Chloropropionic acid 107-94-8 C3H5ClO2 详情 详情
(V) 13521 3-[3-[(Methylsulfonyl)amino]-4-phenoxyphenoxy]propionic acid C16H17NO6S 详情 详情
(VI) 13522 N-(4-Oxo-6-phenoxy-3,4-dihydro-2H-chromen-7-yl)methanesulfonamide C16H15NO5S 详情 详情
(VII) 13523 N-(3-Bromo-4-oxo-6-phenoxy-3,4-dihydro-2H-chromen-7-yl)methanesulfonamide C16H14BrNO5S 详情 详情
(VIII) 13524 N-(3-Amino-4-oxo-6-phenoxy-4H-chromen-7-yl)methanesulfonamide C16H14N2O5S 详情 详情
Extended Information