Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 44540255 | HCID 44540255 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 59416079 | HCID 59416079 | — |
Reaction Steps
Ethyl 6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-1-(4-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (Example 132, 0.225 g, 0.35 mmol) was diluted with 2:1 MeOH:THF (3 mL). A 2 M aq solution of LiOH (0.35 mL, 0.7 mmol) was added and the reaction mixture was heated in the microwave to 100° C. for 15 min. The mixture was conc in vacuo and acidified to approx. pH 3 with 1 N aq HCl. The resultant solid was collected and purified by column chromatography (silica 95:5 methylene chloride/methanol) followed by purification by reverse phase HPLC (C18, 0-95% acetonitrile/water gradient).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08283361B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-68610ee6058745b8bb0bf305a99e52b5 |
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| Source note | uspto-grants-2012_10 |
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