Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate | HCID 151348 | — |
| Reactant | HCID 28370697 | HCID 28370697 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66965860 | HCID 66965860 | — |
Reaction Steps
To a vial containing a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-ylamine in dioxane (0.2 M, 0.10 mL) was added DIPEA (0.5 M in toluene, 0.050 mL) and acetic acid (0.2 M in toluene, 0.12 mL), followed by BOP reagent (0.2 M in DMF, 0.15 mL). After overnight at ambient temperature, the mixture was then diluted by MeOH and the whole was loaded onto a solid phase extraction (SPE) cartridge that contained strong cation exchange (SCX) (1 g media in 6 mL cartridge, United Chemical Technology). Wash-to-waste (5 mL MeOH) was followed by elute-to-collect (5 mL 20:2:1 ethyl acetate-MeOH-Et3N) and, after evaporation of volatiles, the crude was further purified by silica gel column chromatography to N-[2-(2-Chloro-phenyl)-3H-benzoimidazol-5-yl]-acetamide: MS (m/z) 320.02 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222248B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-9b4ba0258fa04eb499af6a1425f45fa2 |
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| Source note | uspto-grants-2012_07 |
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