Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamate | HCID 56643603 | — |
| Reactant | HCID 66671536 | HCID 66671536 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 66793822 | HCID 66793822 | 98.5% |
Reaction Steps
The compound (233 mg, 0.58 mmol) obtained in Example 100c was dissolved in 6.0 mL of dichloromethane, and 1-[2-(methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (227 mg, 0.64 mmol) and triethylamine (163 μL, 1.17 mmol) were added. The mixture was ice cooled, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (168 mg, 0.88 mmol) and 4-(dimethylamino)pyridine (10 mg, 0.082 mmol) were added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate was added to the reaction mixture to dilute the mixture, and the organic layer was washed with water and a saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried with anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure, and the resulting yellow oily substance was purified by NH silica gel chromatography (n-hexane:ethyl acetate, 50:50→20:80, v/v) to give the title compound (420 mg; yield, 98%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08476253B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-f35da47e78fb4bffad6665eaea9c5b3b |
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| Source note | uspto-grants-2013_07 |
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