関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Benzocaine | HCID 2337 | — |
| 反応物 | Methyl indole-6-carboxylate | HCID 639844 | — |
| 反応物 | 4-{[1-(3,5-Dichloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid | HCID 16051865 | — |
| 反応物 | Methyl indoline-6-carboxylate | HCID 16244446 | — |
| 反応物 | 1-[(tert-butoxy)carbonyl]-2,3-dihydro-1H-indole-6-carboxylic acid | HCID 18354849 | — |
| 反応物 | 1-tert-butyl 6-methyl 2,3-dihydro-1H-indole-1,6-dicarboxylate | HCID 66575048 | — |
| 生成物 | 4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester | HCID 68696720 | — |
反応手順
4-{[1-(3,5-Dichloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=488.9 (M−H), was prepared in analogy to example 14, steps 1 to 6. Step 1 was performed starting from 1H-indole-6-carboxylic acid methyl ester, which was reduced to 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (see also example 34). This was protected in step 2 to 2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester, which was then hydrolyzed to 2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester in step 3. Step 4 was performed using 4-amino-benzoic acid ethyl ester, yielding 4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester. This was reacted with 3,5-dichloro-benzenesulfonyl chloride in step 5, yielding 4-{[1-(3,5-dichloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, which was hydrolyzed in step 6.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07713996B2 |
|---|
| 出典データセット | uspto-grants-2010_05 |
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| ORD ID | ord-996da454903e4198938d665a92b005cb |
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| 出典メモ | uspto-grants-2010_05 |
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