Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 59570969 | HCID 59570969 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59571072 | HCID 59571072 | 93.1% |
Reaction Steps
A mixture of (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)-N-{5-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyrazin-2-yl}propanamide (118 mg) in THF (10 mL) was added 1 M hydrochloric acid (10 mL) at room temperature, followed by stirring for 2 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. After concentration, the obtained crude product was purified by silica gel column chromatography (wetting with hexane:ethyl acetate=1:1, chloroform:methanol=1:0-10:1) to obtain (2R)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-N-[5-(2-hydroxyethyl)pyrazin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanamide (94 mg) as a white amorphous substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08329707B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-65b56eec76894a22abdf5e6081886efb |
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| Source note | uspto-grants-2012_12 |
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