HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 5-Bromo-2-{[(2,4-difluorophenyl)methyl]oxy}-N-(3-methyl-4-isoxazolyl)-4-(4-morpholinylmethyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HOAt | HCID 181649 | — |
| Reactant | 3-Methyl-1,2-oxazol-4-amine hydrochloride | HCID 13804285 | — |
| 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}-N-(3-methyl-4-isoxazolyl)-4-(4-morpholinylmethyl)benzamide | HCID 66610654 | — |
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 diisopropylethylamine (0.12 ml, 0.68 mmol), 1-hydroxy-7-azabenzotriazole (55.4 mg, 0.41 mmol), 3-methyl-4-isoxazolamine hydrochloride (39.9 mg, 0.41 mmol) and EDC (98 mg, 0.51 mmol). The reaction was stirred for 18 hours. The solvent was removed in vacuo and the residue was purified by column chromatography (SiO2; ethyl acetate) to yield 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-db44c56f6bea4df2aa6978536779d0e8 |
| Source note | uspto-grants-2016_06 |