HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202898Generated: October 31, 2026
Propionic Acid → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one
https://huagongshe.com/reaction/2202898
Participants
| Role | Name | HCID | Charge |
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| Reactant | Propionic Acid | HCID 1032 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| 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 | 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one | HCID 71660914 | — |
Reaction Steps
A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (90 mg), HATU (106 mg), propionic acid (0.040 ml), N,N-diisopropylethylamine (0.136 ml) and DMF (2 ml) was stirred at room temperature under a dry atmosphere (CaCl2 tube) 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 resulting residue was dissolved in AcOH (2 ml), and the mixture was stirred at 90° 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 EtOAc/MeOH to give the title compound (44.9 mg) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365540B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-5352d093cd54494593ea81ec5a336de4 |
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| Source note | uspto-grants-2016_06 |
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