Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | N-but-3-enyl-2-[3-cyclohexyl-2-[2-(2,4-dimethyl-thiazol-5-yl)-quinolin-6-yl]-6-(prop-2-ene-1-sulfonyl-aminocarbonyl)-indol-1-yl]-acetamide | HCID 59549089 | — |
| Catalyst | HCID 178458314 | HCID 178458314 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 68506955 | HCID 68506955 | — |
Reaction Steps
A solution of intermediate 17-5 (260 mg, 0.373 mmol) in DCE (400 mL) was bubbled through with N2 during 2 h. Hoveyda-Grubbs 1st generation catalyst (45 mg, 0.2 eq) was next added and the reaction mixture was heated at 80° C. under N2 overnight. The reaction mixture was then concentrated under reduced pressure and purified by flash chromatography (CH2Cl2/methanol 95:5) to give the desired product 18 as a gray powder after recrystallization from CH2Cl2/isopropyl ether; m/z=668 (M+H+), NMR (DMSO-d6): δ (ppm) 1.20-1.30 (m, 3H), 1.63-1.93 (m, 9H), 2.34 (m, 2H), 2.66 (m, 1H), 2.67 (s, 3H), 2.73 (s, 3H), 3.23 (m, 2H), 4.50 (s, 2H), 5.64 (m, 2H), 7.45 (m, 1H), 7.73-8.12 (m, 6H), 8.47 (broad s, 1H, NHCO), 8.54 (d, J=8.4 Hz, 1H), 11.47 (broad s, 1H, NHSO2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08524716B2 |
|---|
| Source dataset | uspto-grants-2013_09 |
|---|
| ORD ID | ord-00af4674bb9c4e6aa0f722da9a0ce038 |
|---|
| Source note | uspto-grants-2013_09 |
|---|
