HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 68444433, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-Hydroxyazetidine hydrochloride | HCID 2759290 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid | HCID 66599213 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68444433 | HCID 68444433 | 91% |
Reaction Steps
To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (200 mg, 0.65 mmol) and azetidin-3-ol hydrochloride (70.7 mg, 0.65 mmol) in THF (6 mL) at 0° C. were added 1-hydroxybenzotriazole hydrate (100.8 mg, 0.65 mmol), N-ethyldiisopropylamine (281.7 μl, 1.613 mmol) and N-(3-dimethylaminopropy)-N′-ethylcarbodiimidazole hydrochloride (126.2 mg, 0.65 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=3:1 to 1:4) afforded the title compound (215 mg, 91%) as a colourless oil. MS: m/e=366.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08877783B2 |
| Source dataset | uspto-grants-2014_11 |
| ORD ID | ord-976ad908a7f0464b9ff1586869007c22 |
| Source note | uspto-grants-2014_11 |