Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 7-[(4'-Trifluoromethyl-biphenyl-2-carbonyl)-amino)-quinoline-3-carboxylic acid | HCID 10296719 | — |
| Reactant | HCID 22736884 | HCID 22736884 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 9808866 | HCID 9808866 | 32.6% |
Reaction Steps
7-[(4′-Trifluoromethyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid (250 mg, 0.57 mmol) was combined with di-(2-pyridyl)-methylamine hydrochloride (126 mg, 0.57 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (121 mg, 0.69 mmol), 1-hydroxybenzotriazole (85 mg, 0.63 mmol), and triethylamine (0.32 ml, 2.3 mmol) in 3 ml of dichloromethane. After stirring overnight at ambient temperature, the reaction mixture was diluted with 75 ml of dichloromethane, and the organic phase washed sequentially with water (2×40 ml), and brine, and then dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide a yellow residue. This material was purified by preparative thin-layer-chromatography on silica eluting with 3% methanol in dichloromethane. The product containing band was collected and eluted with 5% methanol in ethyl acetate to afford 112 mg of the title compound as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06369075B1 |
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| Source dataset | uspto-grants-2002_04 |
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| ORD ID | ord-269d031d311948cbb56dcdd2ce394931 |
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| Source note | uspto-grants-2002_04 |
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