Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Propionic Acid | HCID 1032 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 21300450 | HCID 21300450 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67099223 | HCID 67099223 | 54.5% |
Reaction Steps
To a solution of 6-chloro-5-(chloromethyl)-1-[4-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)phenyl]-2-ethyl-1H-benzimidazole (step 2, 403 mg, 0.86 mmol) in N,N-dimethylformamide (10 ml) was added propionic acid (0.06 ml, 0.86 mmol) and NaHCO3 (144 mg, 1.72 mmol) at room temperature. The mixture was stirred at 60° C. for 7 h. The mixture was added water (50 ml) and extracted with ethyl acetate(100 ml). The organic layer was washed with brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (8:1/4:1) to afford 235 mg (53%) of the title compound as pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07141580B2 |
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| Source dataset | uspto-grants-2006_11 |
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| ORD ID | ord-76e3ea8f7eeb490b8a05d8c4f931a5a9 |
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| Source note | uspto-grants-2006_11 |
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