HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-(4-Fluoro-3-methylphenyl)-1-{[3-(4-methylphenyl)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-(4-Methylphenyl)isoxazole-4-carboxylic acid | HCID 58828797 | — |
| Reactant | 3-(4-Fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochloride | HCID 68685567 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(4-Fluoro-3-methylphenyl)-1-{[3-(4-methylphenyl)isoxazol-4-yl]carbonyl}pyrrolidin-3-ol | HCID 59170246 | 80.9% |
Reaction Steps
A solution of 3-(4-fluoro-3-methylphenyl)pyrrolidin-3-ol hydrochloride (9 mg, 0.039 mmol), TBTU (15 mg, 0.047 mmol, 1.2 equ.) and N-ethyl-N-isopropylpropan-2-amine (14 μL, 0.079 mmol, 2 equ.) in DMF (0.3 mL) was added to 3-(4-methylphenyl)isoxazole-4-carboxylic acid (8 mg, 0.039 mmol) and the reaction mixture was stirred at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (12 mg). MS (ESI, pos. ion) m/z calcd for C22H21FN2O3: 380.1536, found 380.1532.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666888B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-9220ebb7b4974d1b91cd6e6545be8cee |
| Source note | uspto-grants-2010_02 |