HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202958Generated: November 4, 2026
Diisopropylethylamine → 4-((4-Chlorobenzyl)oxy)-1-(2-((1RS,2RS)-2-fluorocyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one
https://huagongshe.com/reaction/2202958
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| Reactant | cis-2-Fluorocyclopropanecarboxylic acid | HCID 9793716 | — |
| 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-((1RS,2RS)-2-fluorocyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one | HCID 121386231 | 15.8% |
Reaction Steps
A mixture of 1-(4-amino-3-(methylamino)phenyl)-4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (200 mg), HATU (224 mg), cis-2-fluoro-cyclopropanecarboxylic acid (100 mg), N,N-diisopropylethylamine (288 μl) and DMF (4 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 residue was dissolved in AcOH (4.0 ml) and stirred at 90° C. for 1 h. After AcOH was evaporated, the residue was purified by NH silica gel column chromatography (hexane/EtOAc). The resulting solid was recrystallized from EtOH to give the title compound (37.6 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-63131c222d624cf2ad747ea227d03590 |
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| Source note | uspto-grants-2016_06 |
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