HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 3-Aminopyridine | HCID 10009 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid | HCID 66611303 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)-N-3-pyridinylbenzamide | HCID 66611954 | — |
Reaction Steps
To a solution of 5-bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-4-(4-morpholinylmethyl)benzoic acid (may be prepared as described in Description 22; 150 mg, 0.34 mmol) in N,N-dimethylformamide (4 ml) was added 3-aminopyridine (38.3 mg, 0.41 mmol), diisopropylethylamine (0.12 ml, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (55.4 mg, 0.41 mmol) and EDC (98 mg, 0.51 mmol). The mixture was stirred overnight and the solvent removed in vacuo to give a residue. Purification by column chromatography (SiO2; 10% 7M NH3 in methanol/dichloromethane) yielded the title compound as a solid. 162 mg.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365551B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-3239d45288eb480888f1128b84d9cf8d |
| Source note | uspto-grants-2016_06 |