HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(5-methylpyridin-2-yl)pyrrolidin-3-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | 3-(3-Chloro-4-methoxyphenyl)-isoxazole-4-carboxylic acid | HCID 59170145 | — |
| Reactant | 3-(5-Methylpyridin-2-yl)pyrrolidin-3-ol dihydrochloride | HCID 68687460 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-{[3-(3-Chloro-4-methoxyphenyl)isoxazol-4-yl]carbonyl}-3-(5-methylpyridin-2-yl)pyrrolidin-3-ol | HCID 59170176 | 54.4% |
Reaction Steps
A solution of 3-(3-chloro-4-methoxyphenyl)isoxazole-4-carboxylic acid (10 mg, 0.04 mmol), N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.08 mmol, 2 equ.) and TBTU (15 mg, 0.046 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-(5-methylpyridin-2-yl)pyrrolidin-3-ol dihydrochloride (10 mg, 0.04 mmol). After 1 h at rt the crude product was purified by RP-HPLC. The pure fractions were basified (NaHCO3) and extracted with ethyl acetate, dried (Na2SO4), evaporated and dried in vacuum to yield the title compound (9 mg). MS (ESI, pos. ion) m/z: calcd for C21H20ClN3O4: 413.1142, found 413.1143.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-57b3343abe564b13941c245181b98d49 |
| Source note | uspto-grants-2010_02 |