New synthesis of a late-stage tetracyclic key intermediate of lumateperone
New approaches have been tested for the synthesis of lumateperone intermediates. As a result of these efforts, a novel synthesis of the late-stage tetracyclic key intermediate of lumateperone starting from the commercially available quinoxaline is described. The tetracyclic skeleton was constructed...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2022-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.66 |
| _version_ | 1818523923124322304 |
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| author | Mátyás Milen Bálint Nyulasi Tamás Nagy Gyula Simig Balázs Volk |
| author_facet | Mátyás Milen Bálint Nyulasi Tamás Nagy Gyula Simig Balázs Volk |
| author_sort | Mátyás Milen |
| collection | DOAJ |
| description | New approaches have been tested for the synthesis of lumateperone intermediates. As a result of these efforts, a novel synthesis of the late-stage tetracyclic key intermediate of lumateperone starting from the commercially available quinoxaline is described. The tetracyclic skeleton was constructed by the reaction of 1-trifluoroacetyl-4-aminoquinoxaline with ethyl 4-oxopiperidine-1-carboxylate in a Fischer indole synthesis. The inexpensive starting material, the efficient synthetic steps, and the avoidance of the borane-based reduction step provide a reasonable potential for scalability. |
| first_indexed | 2024-12-11T05:50:46Z |
| format | Article |
| id | doaj.art-d17b83791c4a444e9567ef12d722146c |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-11T05:50:46Z |
| publishDate | 2022-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-d17b83791c4a444e9567ef12d722146c2022-12-22T01:18:49ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-06-0118165365910.3762/bjoc.18.661860-5397-18-66New synthesis of a late-stage tetracyclic key intermediate of lumateperoneMátyás Milen0Bálint Nyulasi1Tamás Nagy2Gyula Simig3Balázs Volk4Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O. Box 100, Hungary Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O. Box 100, Hungary Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O. Box 100, Hungary Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O. Box 100, Hungary Egis Pharmaceuticals Plc., Directorate of Drug Substance Development, 1475 Budapest, P.O. Box 100, Hungary New approaches have been tested for the synthesis of lumateperone intermediates. As a result of these efforts, a novel synthesis of the late-stage tetracyclic key intermediate of lumateperone starting from the commercially available quinoxaline is described. The tetracyclic skeleton was constructed by the reaction of 1-trifluoroacetyl-4-aminoquinoxaline with ethyl 4-oxopiperidine-1-carboxylate in a Fischer indole synthesis. The inexpensive starting material, the efficient synthetic steps, and the avoidance of the borane-based reduction step provide a reasonable potential for scalability.https://doi.org/10.3762/bjoc.18.66drug substanceindole synthesiskey intermediateprotecting grouptelescoping |
| spellingShingle | Mátyás Milen Bálint Nyulasi Tamás Nagy Gyula Simig Balázs Volk New synthesis of a late-stage tetracyclic key intermediate of lumateperone Beilstein Journal of Organic Chemistry drug substance indole synthesis key intermediate protecting group telescoping |
| title | New synthesis of a late-stage tetracyclic key intermediate of lumateperone |
| title_full | New synthesis of a late-stage tetracyclic key intermediate of lumateperone |
| title_fullStr | New synthesis of a late-stage tetracyclic key intermediate of lumateperone |
| title_full_unstemmed | New synthesis of a late-stage tetracyclic key intermediate of lumateperone |
| title_short | New synthesis of a late-stage tetracyclic key intermediate of lumateperone |
| title_sort | new synthesis of a late stage tetracyclic key intermediate of lumateperone |
| topic | drug substance indole synthesis key intermediate protecting group telescoping |
| url | https://doi.org/10.3762/bjoc.18.66 |
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