Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Chloropyrazine | HCID 73277 | — |
| Reactant | HCID 54025520 | HCID 54025520 | — |
| Catalyst | Zinc bromide | HCID 10421208 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 54218343 | HCID 54218343 | — |
Reaction Steps
To a suspension of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (prepared essentially as described in Example 1, 100 mg in 1 mL chloropyrazine) was added 500 mg zinc bromide and the mixture heated to 150° C. on an oil bath. After 3 hours, the mixture was cooled to room temperature, diluted with ethyl acetate and filtered through diatomaceous earth. The volatile organics were removed in vacuo and the residue dissolved in ethyl acetate, washed with water and the organic portion dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 1:1) to give the title compound (12 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06150352 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-e55501bd3aa24cef9989e7c24aaa2c94 |
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| Source note | uspto-grants-2000_11 |
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