HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → 4-((4-Chlorobenzyl)oxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| 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 | 4-(4-Chlorobenzyloxy)-1-(4-amino-3-(methylamino)phenyl)pyridin-2(1h)-one | HCID 89690258 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-((4-Chlorobenzyl)oxy)-1-(1,2-dimethyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 89690970 | — |
Reaction Steps
HATU (321 mg) was added to a solution of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (250 mg), N,N-diisopropylethylamine (0.367 ml) and AcOH (0.044 ml) in DMF (3 ml) at room temperature. The mixture was stirred at room temperature for 2 h. Water (6 ml) was added to the mixture. The precipiate was collected by filtration and dissolved to AcOH (3 ml). The mixture was stirred at 80° C. for 1 h. After evaporation of the solvent, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH to give the title compound (140 mg) as a pale pink solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-0e8d560f7bf24ff4a4956af4f0da0788 |
| Source note | uspto-grants-2016_06 |