Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 2-Morpholinoethylamine | HCID 408285 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 68621686 | HCID 68621686 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 46235474 | HCID 46235474 | 53.2% |
Reaction Steps
To a stirred solution of 6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxylic acid (6 mg, 14 μmol), morpholinoethyl amine (3 μl, 17 μmol), HOBt (3 mg, 17 μmol), and triethylamine (4 μl, 28 μmol) in N,N-dimethylformamide (0.3 Ml), was added EDCI (4 mg, 21 μmol). After the mixture was stirred at 70° C. for 12 h, the mixture was cooled to room temperature, and ethyl acetate and saturated sodium bicarbonate solution were added. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated in ethyl acetate/hexane to give N-(2-morpholinoethyl)-6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxamide (4 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08754209B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-48706420013741bd867b3a6916555443 |
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| Source note | uspto-grants-2014_06 |
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