Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzenesulfonic Acid | HCID 7371 | — |
| Reactant | Crenolanib | HCID 10366136 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 670220-93-6 | HCID 18435899 | 89.5% |
Reaction Steps
The compound, 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine (2.44 9, 5.5 mmol, 1 equivalent) and ethanol (24 mL, 10 volumes) were added to a 100 mL round bottom flask. The solution was heated to reflux to dissolve the starting material and then cooled to room temperature. A solution of benzenesulfonic acid (918 mg, 5.2 mmol, 0.95 equivalents) in ethanol (5 mL, 2 volumes) was charged and the reaction was heated to reflux for ˜30 minutes. The reaction was cooled to 20–30° C. and allowed to granulate for 16–32 hours. The material was then filtered and dried under vacuum with a slight nitrogen bleed to afford 1-{2-[5-(3-Methyl-oxetan-3-ylmethoxy)-benzoimidazol-1-yl]-quinolin-8-yl}-piperidin-4-ylamine benzenesulfonate (2.8 g, 85% yield) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07183414B2 |
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| Source dataset | uspto-grants-2007_02 |
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| ORD ID | ord-bbb3abcd4f6644ca87d9d749e729bd4a |
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| Source note | uspto-grants-2007_02 |
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