Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | HCID 68622334 | HCID 68622334 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68622096 | HCID 68622096 | 47.3% |
Reaction Steps
To a stirred solution of 6-(4-nitrophenyl)-1H-indazole-3-carboxylic acid (140 mg, 0.5 mmol), methyl amine hydrochloride (45 mg, 0.6 mmol), HOBt (80 mg, 0.6 mmol), and triethylamine (0.3 Ml, 2 mmol) in N,N-dimethylformamide (5 Ml), was added EDCI (142 mg, 0.7 mmol). 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 to give N-methyl-6-(4-nitrophenyl)-1H-indazole-3-carboxamide (70 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08754209B2 |
|---|
| Source dataset | uspto-grants-2014_06 |
|---|
| ORD ID | ord-a1bbeebb73444b27aabce70172a6f8f6 |
|---|
| Source note | uspto-grants-2014_06 |
|---|
