Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | (5-{2-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid | HCID 45138482 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 178470738 | HCID 178470738 | — |
Reaction Steps
To a solution of (5-{2-[(cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid (0.099 g, 0.22 mmol) in EtOH (1 mL) was added thionyl chloride (0.16 mL, 2.19 mmol), and the reaction was stirred at 80° C. overnight. The mixture was diluted with CH2Cl2 and H2O, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give (5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-hydroxy-pyridin-3-yl)-acetic acid ethyl ester. The ester was hydrolyzed to the acid as described in Example 3, Step 7.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08049015B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-5813404ca161462dad468ab59067e465 |
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| Source note | uspto-grants-2011_11 |
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