HuagongsheHuagongshe Chemistry Print Report · For research reference only
Morpholine → [4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| 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 | 4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid | HCID 90273390 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | [4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanone | HCID 77106365 | 80.64% |
Reaction Steps
To a solution of 4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid (260 mg, 0.735 mmol) and HATU (418 mg, 1.10 mmol) in DMF (10.0 mL) were added morpholine (77 mg, 0.88 mmol) and DIPEA (0.4 mL, 2.205 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into ice cold water, extracted with EtOAc (100 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. Crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 100% EtOAc to afford 250 mg (yield: 80.64%) of the title compound as pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09321748B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-36e4b4f9d8564a59bf7dea2c6e0d4189 |
| Source note | uspto-grants-2016_04 |