HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-vinyl-2-pyrrolidone → 3-Chloro-8-methoxy-7-[1-(2-oxopyrrolidin-1-yl)vinyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N-vinyl-2-pyrrolidone | HCID 6917 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-chloro-8-methoxy-11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-7-yl trifluoromethanesulfonate | HCID 87738200 | — |
| Catalyst | HCID 178418807 | HCID 178418807 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-Chloro-8-methoxy-7-[1-(2-oxopyrrolidin-1-yl)vinyl]-5,10-dihydro-11h-dibenzo[b,e][1,4]diazepin-11-one | HCID 69217774 | — |
Reaction Steps
A mixture of Example 516A, 1-vinyl-2-pyrrolidinone, Pd(dppf)Cl2-CH2Cl2, and triethylamine in DMF was heated at 110° C. overnight, cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered and concentrated. The concentrate was purified by column chromatography on silica gel using a solvent gradient that increased from 1 to 4% methanol in dichloromethane to give the title compound. MS (ESI) m/e 384 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07456169B2 |
| Source dataset | uspto-grants-2008_11 |
| ORD ID | ord-ef4269893cc14acf92ab779d66eb474b |
| Source note | uspto-grants-2008_11 |