Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 86712108 | HCID 86712108 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86712107 | HCID 86712107 | 22.5% |
Reaction Steps
A mixture of methyl 6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (Intermediate 53, 0.16 g) and lithium hydroxide monohydrate (0.526 g) in dioxane (10 mL) and water (2.5 mL) was irradiated in the microwave at 135° C. for 45 minutes. After cooling, the mixture was diluted with methanol, acidified with formic acid and evaporated in vacuo. The residue was azeiotroped with a mixture of toluene and ethanol and the residue was triturated with 20% methanol in DCM and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica, eluting with DMAW-60. The resultant solid was further purified by HPLC (C18) to give 6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylic acid (0.035 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09187494B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-d468aa42df5d48df80f76b6d1acad011 |
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| Source note | uspto-grants-2015_11 |
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