HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (5-{[(5-Benzyl-[1,3,4]oxadiazole-2-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamide | HCID 22475372 | — |
| Reactant | 5-Benzyl-1,3,4-oxadiazole-2-carboxylic acid | HCID 58081236 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (5-{[(5-Benzyl-[1,3,4]oxadiazole-2-carbonyl)-amino]-methyl}-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester | HCID 58081289 | — |
Reaction Steps
A mixture of Benzyl-[1,3,4]oxadiazole-2-carboxylic acid (2.4 g, 11 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (2.8 g, 11 mmol), HATU (5.5 g, 15 mmol) and DIPEA (7.8 mL, 45 mmol) in 20 mL DMF was stirred at room temperature for 16 h. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1 N aq. HCl. The organic layer was dried over MgSO4 and evaporated in vacuo. The crude product was purified by preparative HPLC (Waters Sunfire Prep C18 PBD 5 um, 30×100 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min). HPLC (method C) RtA=3.114.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09290485B2 |
| Source dataset | uspto-grants-2016_03 |
| ORD ID | ord-b333a0bb649d4925bfa25b215fc0be7d |
| Source note | uspto-grants-2016_03 |