Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 66685618 | HCID 66685618 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 56656141 | HCID 56656141 | 19.8% |
Reaction Steps
A mixture of methyl 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 45, 0.130 g) and lithium hydroxide (0.105 g) in dioxane (3 mL) and water (1 mL) was heated at 90° C. for 20 hours. After cooling, the mixture was diluted with water (20 mL) and acidified to pH5-6 with formic acid. This was extracted into ethyl acetate. The combined organic layers were dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM, with a gradient of 0-10%. The product was triturated with diethyl ether/ethyl acetate (1:1) to give 7-[2-(3-diethylaminopropyl)-4-fluorobenzenesulfonylamino]-4H-furo[2,3-c]chromene-6-carboxylic acid (0.025 g) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09266896B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-e81852616ae54289840f31ad024c9009 |
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| Source note | uspto-grants-2016_02 |
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