HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → N-methyl-5-nitro-1H-indazole-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | 5-nitro-1H-indazole-3-carboxylic Acid | HCID 7144652 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | N-methyl-5-nitro-1H-indazole-3-carboxamide | HCID 45810073 | 63% |
Reaction Steps
To a solution of compound 54 (100 mg, 0.483 mmol), methylamine hydrochloride (52.2 mg, 0.773 mmol), HOBt (130 mg, 0.966 mmol) and DIEA (0.34 mL, 1.95 mmol) in N-methylpyrrolidinone was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (148 mg, 0.773 mmol). The reaction was stirred at room temperature for 2 hrs and diluted with 10 mL of ethyl acetate. The mixture was washed with water and a yellow solid precipitated. The precipitate was collected by filtration to give compound 55 (67 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08546404B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-9a82de54f3a544d799cc08ca0340dcfa |
| Source note | uspto-grants-2013_10 |