Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 59426351 | HCID 59426351 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59425155 | HCID 59425155 | 92% |
Reaction Steps
A mixture of N-(2-acetoxyethyl)-N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide (compound 815, 164 mg, 0.360 mmol) and lithium hydroxide hydrate (45 mg, 1.07 mmol) in 5 mL THF/1 mL water was warmed to 60° C. overnight. The mixture was cooled and poured into ethyl acetate (50 mL). This was washed with water (50 mL) and brine (20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to afford a solid. The solid was triturated with ether, collected by filtration and dried under high vacuum to afford N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]-N-(2-hydroxyethyl) methanesulfonamide, compound 828 (137 mg, 0.331 mmol, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08013006B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-f5ac835bc66347b19aaf8f5a1eaad858 |
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| Source note | uspto-grants-2011_09 |
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