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【结 构 式】 
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【分子编号】13523 【品名】N-(3-Bromo-4-oxo-6-phenoxy-3,4-dihydro-2H-chromen-7-yl)methanesulfonamide 【CA登记号】 |
【 分 子 式 】C16H14BrNO5S 【 分 子 量 】412.2609 【元素组成】C 46.62% H 3.42% Br 19.38% N 3.4% O 19.4% S 7.78% |
合成路线1
该中间体在本合成路线中的序号：(VII)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 |