참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Sodium borohydride | HCID 4311764 | — |
| 반응물 | Vilazodone | HCID 6918314 | — |
| 반응물 | 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile | HCID 10220528 | — |
| 용매 | Isopropanol | HCID 3776 | — |
| 생성물 | 3-(4-Hydroxybutyl)-1H-indole-5-carbonitrile | HCID 12150985 | — |
반응 단계
As per the process described in CN'932 publication, vilazodone is prepared by reacting 3-(4-chlorobutyryl)-1H-indole-5-carbonitrile with sodium borohydride in isopropanol at reflux temperature, followed by treating the reaction mass with dilute hydrochloric acid and subsequent workup and then subjecting to column chromatography purifications to produce 3-(4-hydroxybutyl)-1H-indole-5-carbonitrile. The hydroxylbutyl intermediate obtained is then subjected to sulfonylation using a sulfonylating agent selected from p-toluenesulfonyl chloride, benzenesulfonyl chloride, methanesulfonyl chloride and trifluoromethanesulfonyl chloride to produce corresponding sulfonylated intermediate, which is then condensed with 5-(1-piperazinyl)benzofuran-2-carboxamide in acetonitrile to produce vilazodone.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US09315456B2 |
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| 출처 데이터셋 | uspto-grants-2016_04 |
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| ORD ID | ord-94ad5614d6ce4816a24f02076f9a69d9 |
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| 출처 메모 | uspto-grants-2016_04 |
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