HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 7-[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(2-thienyl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-[3-({[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate | HCID 86602585 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 7-[5-(5-Chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-3-(2-thienyl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3]thiazine | HCID 11339143 | 8% |
Reaction Steps
To a solution of 2-[3-({[5-(5-chloro-2-fluorophenyl)-1,2,4-oxadiazol-3-yl]methyl}thio)-5-(2-thienyl)-4H-1,2,4-triazol-4-yl]ethyl methanesulfonate (43 mg) in DMF (2 ml) was added sodium hydride (10 mg) at −78° C. while stirring. The mixture was allowed to come to r.t. and stirred for another 3 h before addition of MeOH (1 ml) and concentration onto silica gel. Purification by chromatography on silica gel using DCM:EA:MeOH 70:30:2 as eluent provided 2.8 mg of the title compound. 1H NMR: 8.07 (dd, 1H), 7.56 (m, 1H), 7.51 (dd, 1H), 7.47 (dd, 1H), 7.17-7.23 (m, 2H), 4.86 (dd, 1H), 4.60 (m, 1H), 4.38 (m, 1H), 2.82 (m, 2H)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576077B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-1f72e21a05ad4dd3b14d1f864f1f52b9 |
| Source note | uspto-grants-2009_08 |