Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 86716521 | HCID 86716521 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 76282929 | HCID 76282929 | 68% |
Reaction Steps
To a solution of tert-butyl {1-[4-(6-chloro-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-6.2 (0.075 g, 0.15 mmol) in MeOH (0.65 mL) and DCM (1.0 mL) was added hydrogen chloride (4 M in dioxane, 0.8 mL, 3.2 mmol, 20.0 eq), and the resulting mixture was stirred at room temperature for 19 h. The resulting mixture was added to ice water (50 mL), made alkaline with aqueous sodium hydroxide (2 N), and extracted with EtOAc (2×50 mL). The combined organic phases were dried (Na2SO4 anh.) and concentrated under reduced pressure. The resulting material was recrystallized using diisopropyl ether to give 1-[4-(6-chloro-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutanamine (0.040 g, 68%):
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206185B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-c504c5fba3bd4d20a9937459b78b2f84 |
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| Source note | uspto-grants-2015_12 |
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