HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → 6-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 4-Chloropyridine-2-carboxylic acid | HCID 230890 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | Methyl 6-aminopyridine-2-carboxylate | HCID 13809143 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-[(4-Chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester | HCID 66848725 | 93% |
Reaction Steps
A solution of 4-chloro-pyridine-2-carboxylic acid (16.3 g, 103 mmol), methyl 6-aminopicolinate (3.0 g, 18.6 mmol), (2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 41.1 g, 108 mmol), and N-methyl morpholine (12.5 mL, 108 mmol) in N,N-dimethylformamide was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure, and the residue suspended in acetonitrile. The solid thus obtained was isolated by filtration, washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL) and dried under reduced pressure to afford 6-[(4-chloro-pyridine-2-carbonyl)-amino]-pyridine-2-carboxylic acid methyl ester as a white powder (25.6, 93% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08598360B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-33b4acc0c4884296b59077ea2305fff0 |
| Source note | uspto-grants-2013_12 |