Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Difluoroacetic acid | HCID 9788 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester | HCID 67067961 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Solvent | Cyclohexane | HCID 8078 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178452584 | HCID 178452584 | 72% |
Reaction Steps
To a stirred solution of triphenylphosphine (126 mg, 0.48 mmol) in CCl4 (1 mL) at 0° C. was added triethylamine (67 μL, 0.48 mmol) and difluoroacetic acid (11 μL, 0.18 mmol). After 10 min, {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (80 mg, 0.16 mmol) in 1,2-dichloroethane (1 mL) was added, the temperature raised to 80° C. After 2.5 hours, the reaction mixture was allowed to cool to RT and the solution was directly subjected to flash chromatography (SiO2, 40% ethyl acetate in cyclohexane) to give the title compound as a pale yellow solid (64 mg, 72%). LCMS (Method G): RT=3.93 min, [M+H]+=558.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546376B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-e4bd31b635ac4d2889f5200787b21705 |
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| Source note | uspto-grants-2013_10 |
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