- New and convergent synthesis of AZD 4547
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A practical and convergent synthetic route of AZD 4547 was developed successfully. The intermediate 5-(3,5-dimethoxyphenylethyl)-1H-pyrazol-3-amine (7) was prepared from 3,5-dimethoxybenzaldehyde through 6 simple steps in 52.3% yield. Another intermediate 4-((3S,5R)-3,5-dimethylpiperazin-1-yl)benzoic acid (14) was synthesized from ethyl 4-fluorobenzoate and (2R,6S)-2,6-dimethylpiperazine in 62% yield over 2 steps. Finally, AZD 4547 was obtained from 7 and 14 in 73% yield and 99.1% purity. Purification methods of the intermediates and the final product involved in the route were developed.
- Bu, Lehao,Chen, Wenxin,Gao, Lei,Mao, Yongjun,Sun, Cong,Wang, Han
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p. 276 - 282
(2020/06/10)
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- Method for preparing AZD4547, intermediate and preparation method of intermediate
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The invention provides a method for preparing AZD-4547. The method comprises the following steps: (1) preparing a first intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate; (2) preparinga second intermediate 5-[2-(3, 5-dimethoxyphenyl) ethyl]-1H-pyrazole-3-amine by taking the first intermediate as a raw material; and (3) in an alkali-containing organic solvent, carrying out a reaction on a third intermediate 4-((3S, 5R)-3, 5-dimethylpiperazinyl-1-yl) benzoyl chloride and the second intermediate to prepare the AZD-4547. The method has the advantages of accessible raw materials, simple technique, mild reaction conditions, convenient operation, high yield and low cost and can easily implement industrial production. The invention also provides an intermediate 2-cyano-5-(3, 5-dimethoxyphenyl)-3-oxoethyl valerate for preparing AZD-4547 and a preparation method thereof.
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- NOVEL COMPOUNDS
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There is provided a compound of formula (I): or a pharmaceutically acceptable salt thereof. There are also provided processes for the manufacture of a compound of Formula 1, and the use of a compound of Formula 1 as a medicament and in the treatment of cancer.
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Page/Page column 145
(2008/12/06)
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