Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (3S)-3-Amino-3-(2-methylphenyl)propanoic acid | HCID 6934180 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate | HCID 89812860 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 71735293 | HCID 71735293 | 90% |
Reaction Steps
1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.156 mmol) was combined in an oven-dried flask with 3-(S)-amino-3-o-tolyl-propionic acid (84 mg, 0.468 mmol) (commercially available from Combi-Blocks SS-1801) and N,N-dimethylacetamide (1.5 mL) was added with stirring. Solid sodium methoxide (25 mg, 0.468 mmol) was added and the reaction was heated to 150° C. in an oil bath for approximately five hours. The reaction was cooled and the solution diluted with five volumes of water. The solution was acidified to pH 3 with 1M hydrochloric acid to induce precipitation. Filtration of the solid followed by vacuum drying provided the desired product in 90% yield. LC-MS ESI−: 466 (M−1)−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09409892B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-866a144ad9314e23ac8dba253b4a0d58 |
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| Source note | uspto-grants-2016_08 |
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