HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lawesson's reagent → N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide | HCID 178426725 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-thioxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide | HCID 178426726 | 57.1% |
Reaction Steps
The title compound is analogously synthesized as described for 7-[2-(6-{4-cyano-phen-1-yl}-3H-imidazo[4,5-b]pyridin-2-yl)-ethyl]-azepan-2-thione (compound A2) from 180 mg of N-(2-fluoro-4-methyl-phenyl)-4-{2-[2-(7-oxo-azepan-2-yl)-ethyl]-3H-imidazo[4,5-b]pyridin-6-yl}-benzenesulfonamide (compound B8) and 146 mg of Lawesson's reagent at 100° C. for 3 hours in 20 ml of dioxane. Purification by chromatography on flash silica gel (eluent gradient: dichloromethane/0-10 vol. % ethanol) affords 106 mg of the title compound as a colorless solid of m.p. 271° C. ESI-MS: 538.2 (MH+). TLC: Rf=0.40 (dichloromethane/ethanol 10:1 parts by volume).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790710B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-2b763e6cfa7c435ca32f53d519283ba0 |
| Source note | uspto-grants-2010_09 |