Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lansoprazole | HCID 3883 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 85900220 | HCID 85900220 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59769506 | HCID 59769506 | 68.6% |
Reaction Steps
To a solution of 2-[(chlorocarbonyl)(phenyl)amino]ethyl acetate (0.58 g) prepared in the same way as in Synthetic Example 25 in tetrahydrofuran (10 mL) were added 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]-1H-benzimidazole (0.73 g), triethylamine (0.558 mL) and 4-dimethylaminopyridine (0.024 g), and stirred at 60° C. for 15 hrs. To the reaction solution was added ethyl acetate (30 mL), and washed with water (50 mL) and saturated brine (50 mL), and then, dried over anhydrous sodium sulfate, followed by concentrating under reduced pressure. The residue was purified with flash silica gel column chromatography (eluted with acetone:hexane=1:4, then 3:2). The purified material was crystallized from diethyl ether to give title compound as white solid (0.779 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08449911B2 |
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| Source dataset | uspto-grants-2013_05 |
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| ORD ID | ord-5c19b1df14824592a08a8cb04795ad9f |
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| Source note | uspto-grants-2013_05 |
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