Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride | HCID 11324902 | — |
| Reactant | 8-Bromoquinolin-3-amine | HCID 22674161 | — |
| Product | HCID 22674069 | HCID 22674069 | — |
Reaction Steps
White crystals (180 mg) were obtained in the same manner as in Example 1, except using 145 mg (0.65 mmol) of 3-amino-8-bromoquinoline (Preparation Example 5) and 277 mg (0.85 mmol) of 1,2,3,4-tetrahydro-2-(trifluoroacetyl)isoquinoline-7-sulfonyl chloride. To the crystals were added ethanol (20 ml) and 1 N sodium hydroxide aqueous solution (0.5 ml), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 1 N hydrochloric acid (0.4 ml), followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. To the resulting residue were added pyridine (0.5 ml) and acetic anhydride (0.014 ml), followed by stirring at room temperature for 1 hour. Brine was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, to give 113 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06787534B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-745db91c5cbe48a9a5d1e368e477d489 |
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| Source note | uspto-grants-2004_09 |
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