Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | Glycine, N-methyl-, methyl ester, hydrochloride (1:1) | HCID 83544 | — |
| Reactant | HCID 54025520 | HCID 54025520 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 53873218 | HCID 53873218 | — |
Reaction Steps
To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (53 mg in 2 mL dry methylene chloride) at 0° C. was added phosgene (0.077 mL of a 1.93 M solution in toluene) followed by 0.016 mL of pyridine and the mixture stirred for 1 hour at 0° C. At this time, 70 mg of sarcosine methyl ester hydrochloride was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was diluted with ethyl acetate (15 mL) and the reaction quenched by the addition of 10% citric acid. The organic portion was concentrated in vacuo to provide the crude title compound.
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-ef41914e757044989d741adf70e3a890 |
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| Source note | uspto-grants-2000_11 |
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