Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | PyBroP | HCID 2733179 | — |
| Reactant | tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate | HCID 21940085 | — |
| Reactant | HCID 57652025 | HCID 57652025 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66738155 | HCID 66738155 | — |
Reaction Steps
To 1-(2-chloro-phenyl)-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid described above (320 mg, 1.10 mmol) in methylene chloride (10 mL) was added bromotrispyrrolidinophosphonium hexafluorophosphate (770 mg, 1.65 mmol). The reaction was stirred for 10 minutes and then 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (320 mg, 1.10 mmol) followed by diisopropylethylamine (0.60 mL, 3.30 mmol) were added. The reaction was stirred at room temperature overnight. The crude mixture was diluted in methanol (100 mL), loaded onto silica gel and purified using Isco chromatography (eluting with ethyl acetate and hexanes) to give 4-(4-{[1-(2-chloro-phenyl)-3-trifluoromethyl-1H-pyrazole-carbonyl]-amino}-phenyl)-piperidine-1-carboxylic acid tert-butyl ester. The NMR spectrum obtained on the sample is compatible with its structure.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08058299B2 |
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| Source dataset | uspto-grants-2011_11 |
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| ORD ID | ord-b0d95f34ca5640efa757b7681a8267d1 |
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| Source note | uspto-grants-2011_11 |
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