Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium methanolate methanol | HCID 23694274 | — |
| Reactant | 3-Amino-2,2-difluoropropanoic acid--hydrogen chloride (1/1) | HCID 50998843 | — |
| Reactant | Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate | HCID 89812860 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 89813075 | HCID 89813075 | 51% |
Reaction Steps
1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (75 mg, 0.234 mmol) and 3-Amino-2,2-difluoro-propionic acid hydrochloride (122 mg, 0.75 mmol) were placed in a CEM 10 mL Microwave vessel and sodium methoxide-methanol solution (0.5M; 3 mL, 1.5 mmol) was added via syringe. The vessel was sealed and heated to 130° C. in a CEM microwave apparatus for 150 minutes. The reaction mixture was diluted with water and treated with 1N hydrochloric acid and extracted three times with ethyl acetate then dried over sodium sulfate. The solvent was removed in vacuo to provide the title compound as an orange solid in 51% yield. MS ESI(−) m/e: 412.1027 (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-8e922ca36e654de786a4a363f027da9f |
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| Source note | uspto-grants-2016_08 |
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