HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-hydroxy-N-methoxy-N-methylpicolinamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | 5-Hydroxypyridine-2-carboxylic acid | HCID 268740 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-hydroxy-N-methoxy-N-methylpicolinamide | HCID 86688981 | 87% |
Reaction Steps
To a suspension of 5-hydroxypicolinic acid (1.0 eq), HATU (1.2 eq) and N-methoxymethanamine hydrochloride (1.2 eq) in dry DMF was added DIEtOAc (2.5 eq) dropwise at rt. The mixture was then stirred overnight at rt. After addition with water, the mixture was extracted with CH2Cl2. The extract was dried, concentrated, and purified by column chromatography to give the desired product (87% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09309211B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-924bf59f75734bb8a1190c44dcd8996f |
| Source note | uspto-grants-2016_04 |