HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(2-Chlorophenyl)-1-{[3-(4-methoxyphenyl)isoxazol-4-yl]carbonyl}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-Pyrrolidinol, 3-(o-chlorophenyl)-, hydrochloride | HCID 3051543 | — |
| Reactant | 3-(4-Methoxyphenyl)isoxazole-4-carboxylic acid | HCID 59170121 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(2-Chlorophenyl)-1-{[3-(4-methoxyphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol | HCID 59170151 | 75.2% |
Reaction Steps
A solution of 3-(4-methoxyphenyl)isoxazole-4-carboxylic acid (7 mg, 0.03 mmol), N-ethyl-N-isopropylpropan-2-amine (16 μL, 0.09 mmol, 3 equ.) and TBTU (12 mg, 0.036 mmol, 1.2 equ.) in DMF (0.3 mL) was added to 3-(2-chlorophenyl)pyrrolidin-3-ol hydrochloride (7 mg, 0.03 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 C21H19ClN2O4: 398.1033, found 398.1036.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-f8054cdbabf746ddb05480a60bbbf5b9 |
| Source note | uspto-grants-2010_02 |