HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl N-(triethylammoniosulfonyl)carbamate → 5-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl N-(triethylammoniosulfonyl)carbamate | HCID 2724994 | — |
| Reactant | 6-isobutyl-5-methyl-nicotinic acid N'-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide | HCID 68765289 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-[5-(4-Allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine | HCID 68766160 | 94.6% |
Reaction Steps
A solution of 6-isobutyl-5-methyl-nicotinic acid N′-(4-allyloxy-3,5-dimethyl-benzoyl)-hydrazide (89 mg, 0.224 mmol) and Burgess reagent (162 mg, 0.68 mmol) in THF (4 mL) is heated in a microwave oven at 110° C. for 6 min. The mixture is diluted with EA (15 mL) and washed with 1M aq. NaH2PO4 (5 mL), 1M aq. NaOH (5 mL) and water (5 mL). The org. phase is dried (MgSO4), filtered and evaporated to provide crude 5-[5-(4-allyloxy-3,5-dimethyl-phenyl)-[1,3,4]oxadiazol-2-yl]-2-isobutyl-3-methyl-pyridine (80 mg); LC-MS: tR=1.07 min, [M+1]+=378.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288554B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-c396a6b414cc444eb45d04b282d1d83e |
| Source note | uspto-grants-2012_10 |