HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-[(4-Morpholin-4-ylphenyl)amino]-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzenamine, 4-(4-morpholinyl)- | HCID 75655 | — |
| Reactant | 3-Chloro-4-phenyl-1-[(pyridin-3-yl)methyl]-1H-pyrrole-2,5-dione | HCID 69145172 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 3-[(4-Morpholin-4-ylphenyl)amino]-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione | HCID 11236023 | 27% |
Reaction Conditions
| Temperature | 130 °C |
|---|
Reaction Steps
4-Morpholinoaniline (0.94 mmol, 178 mg) dissolved in dry CH3CN (2 mL) was added to crude 3-chloro-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione (0.47 mmol, 140 mg) and the reaction mixture was subjected to microwave heating single node 130° C. for 10 min. 0.3 mL water was added and the reaction mixture was purified using HPLC (57% 0.1M ammonium acetate buffer: 43% CH3CN→100% CH3CN, 20 mL/min) to give 56 mg (27%) of the title compound. 1H NMR (400 MHz, CD3CN) δ 8.63 (d, 1H), 8.51 (dd, 1H), 7.81-7.73 (m, 1H), 7.36-7.31 (m, 1H), 7.16-7.11 (m,1H), 7.10-7.04 (m, 2H), 6.99-6.93 (m, 2H), 6.69-6.64 (m, 2H), 6.59-6.53 (m, 2H), 4.75 (s, 2H), 3.74 (t, J=4.8 Hz, 4H), 2.97 (t, J=4.8 Hz, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07432288B2 |
| Source dataset | uspto-grants-2008_10 |
| ORD ID | ord-41681ea0e800449885ba73028c4a9831 |
| Source note | uspto-grants-2008_10 |