HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-{1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indol-3-yl}propan-1-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3-(3-Azidopropyl)-1-[(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indole | HCID 22219737 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-{1-[(6-Chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indol-3-yl}propan-1-amine | HCID 22219739 | 78% |
Reaction Steps
A mixture of 3-(3-azidopropyl)-1-[(6-chloroimidazo-[2,1-b][1,3]thiazol-5-yl)sulfonyl]-5-fluoro-1H-indole (180 mg, 0.41 mmol) and triphenylphosphine (161 mg, 0.62 mmol in THF and water is stirred under nitrogen for 24 h at room temperature and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/2M NH3 in MeOH: 98/2) to afford the title product as an off-white solid, 132 mg (78% yield), mp 139-141° C., identified by NMR and mass spectral analyses.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06770642B2 |
| Source dataset | uspto-grants-2004_08 |
| ORD ID | ord-4dd3be28f1594754921230aa46b7be5f |
| Source note | uspto-grants-2004_08 |