HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylamine → HCID 68891654, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylamine | HCID 674 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| 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 | 5-Bromo-3-fluoro-2-(phenylmethoxy)benzoic acid | HCID 68891476 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68891654 | HCID 68891654 | — |
Reaction Steps
2-Benzyloxy-5-bromo-3-fluoro-benzoic acid (product from step 2) (0.2 g, 0.615 mmol) is dissolved in THF (10 ml) and treated with 2M dimethylamine in THF (0.308 ml), N-methylmorpholine (0.270 ml, 2.46 mmol) and HATU (0.234 g, 0.615 mmol) and stirred at room temperature overnight. The reaction mixture is diluted with 2M HCl and extracted with EtOAc (2×), the organic portions are combined washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting crude residue is dry loaded onto silica and purification by flash chromatography eluting with EtOAc affords the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08901134B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-a4f0f271c05b4ac5b70ef256a3a404f4 |
| Source note | uspto-grants-2014_12 |