HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 89702307, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Methyl-1,3-oxazole-5-carboxylic acid | HCID 292311 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| 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 | 1-(4-Amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one | HCID 89690279 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 89702307 | HCID 89702307 | 50% |
Reaction Steps
A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (100 mg), 4-methyl-1,3-oxazole-5-carboxylic acid (37.5 mg), HATU (118 mg) and N,N-diisopropylethylamine (0.154 ml) in DMF (2 ml) was stirred at room temperature for 2 h. The mixture was poured into saturated NaHCO3 solution and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was dissolved in AcOH (2 ml), and the mixture was stirred at 80° C. for 2 h. The mixture was concentrate in vacuo, and purified by NH silica gel column chromatography (MeOH/EtOAc). The resulting solid was washed with EtOAc/hexane to give the title compound (63.4 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-7d77680ea7e740d4ad65ed26efd55009 |
| Source note | uspto-grants-2016_06 |