HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → 17-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 1-{[4-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester | HCID 68412435 | — |
| Catalyst | (1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)ruthenium | HCID 11763533 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | 17-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl ester | HCID 68411307 | 70% |
Reaction Steps
The diene 157 (0.70 g, 1.041 mmol) was dissolved in dry DCE (0.7 L). The solution was put under inert atmosphere (N2) and catalyst (Hoveyda Grubbs 2nd generation, 70 mg, 0.113 mmol) was added to the solution. The reaction mixture was refluxed for 16 h, cooled to room temperature and evaporated on silica by rotary evaporation. The product was purified by flash chromatography (heptane:ethyl acetate 1:1) which gave the title compound (0.466 g, 70%), LRMS (M+H) 645.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07659245B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-0062891b9fc14939a38b833a9d7d072d |
| Source note | uspto-grants-2010_02 |