HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 2-amino-5-bromo-N-methoxy-N-methylnicotinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-Amino-5-bromonicotinic acid | HCID 737445 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-amino-5-bromo-N-methoxy-N-methylnicotinamide | HCID 59699724 | — |
Reaction Steps
To a solution of 2-Amino-5-bromonicotinic acid (1 g, 4.6 mmol) in DMF (15 ml) is added EDC hydrochloride (1.06 g, 5.53 mmol), HOBt (0.747 g, 5.53 mmol), diisopropylethylamine (2 ml, 11.5 mmol) and N-methoxy-N-methylamine hydrochloride (0.54 g, 5.53 mmol), and the resulting solution is stirred at room temperature overnight. The reaction is concentrated in vacuo, and the residue is dissolved in EtOAc, washed with sat. aq. NaHCO3, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (SiO2, 0-10% ethanol in DCM) yields 2-Amino-5-bromo-N-methoxy-N-methyl-nicotinamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268834B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-49a8fb6aa17f4cd4bc6b2a8a58a6dcaf |
| Source note | uspto-grants-2012_09 |