HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 4-((4-Chlorobenzyl)oxy)-1-(2-(cyclopropylmethyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Cyclopropaneacetic acid | HCID 138440 | — |
| 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 | Dimethylformamide | HCID 6228 | — |
| Product | 4-((4-Chlorobenzyl)oxy)-1-(2-(cyclopropylmethyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 89691131 | — |
Reaction Steps
A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (90 mg), HATU (101 mg), N,N-diisopropylethylamine (0.130 ml), cyclopropylacetic acid (0.024 ml) and DMF (2 ml) was stirred at room temperature for 1 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was dissolved in AcOH (2.00 ml), and the mixture was stirred at 90° C. for 2 h. After evaporation, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH to give the title compound (56.3 mg) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-3e04717e477342d2ae1310b8770a9435 |
| Source note | uspto-grants-2016_06 |