Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | HCID 56849102 | HCID 56849102 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 56849227 | HCID 56849227 | 19.2% |
Reaction Steps
In a dried reaction flask, the crude 2-(3-chloro-4-cyanophenyl)-3-cyclopentyl-3,3a,4,5-tetrahydro-2H-pyrazolo[3,4-f]quinoline-7-carboxylic acid (0.4 g, about 0.9 mmol), ethanol amine (0.35 mL, 5.8 mmol), DIEA (0.68 mL, 3.93 mmol) and HATU (1.466 g, 3.856 mmol) were added to a mixed solvent of DMF (4.5 mL) and dichloromethane (4.5 mL). The reaction solution was stirred at room temperature for 4 days and at 30° C. for 16 hr. Water and dichloromethane were added. The mixture was extracted with dichloromethane. The combined organic phase was washed with water and saturated salt water, dried over anhydrous sodium sulfate, and concentrated at reduced pressure to produce a crude yellow solid, which was purified by preparative chromatography to obtain a purified product (80 mg) in 19.2% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946279B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-96d9d50270634d55a82e2560f6c1c723 |
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| Source note | uspto-grants-2015_02 |
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