Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Ethynylpyridin-2-amine | HCID 12422526 | — |
| Reactant | (2-Fluoro-4-(pyridin-2-yloxymethyl)-phenyl)acetohydroximoyl chloride | HCID 72262869 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59255510 | HCID 59255510 | 37.6% |
Reaction Steps
To a tetrahydrofuran (3 mL) solution of the 3-ethynyl-pyridin-2-ylamine (38.4 mg, 0.325 mmol) described in Manufacturing Example 1-2-3 and (2-fluoro-4-(pyridin-2-yloxymethyl)-phenyl)acetohydroximoyl chloride (150 mg, 0.509 mmol) described in Manufacturing Example 204-1-8 was added triethylamine (97.2 μL, 0.697 mmol), which was stirred for 2 hours at 60° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2, then 1:1) to obtain the title compound (46 mg, 24%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07691882B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-69bf1f83c21944ecb0881652426bb3ba |
|---|
| Source note | uspto-grants-2010_04 |
|---|