HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-[4-(5-Methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutanamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate | HCID 86691044 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 1-[4-(5-Methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutanamine | HCID 66665667 | 41.9% |
Reaction Steps
To a mixture of crude tert-butyl {1-[4-(5-methyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl}carbamate (49 mg) in DCM (0.42 mL) and methanol (0.26 mL) was added a solution of 4 M hydrogen chloride in dioxane (0.54 mL) and the mixture was stirred overnight at rt. The mixture was poured onto ice, made alkaline with aqueous sodium hydroxide (2 N) and extracted three times with a mixture of DCM. The combined organic phases were washed with brine, dried and concentrated in vacuo to give 16 mg of the title compound in 42% overall yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08975265B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-d055fd3cf7ce4d48853909c1f92fb0a2 |
| Source note | uspto-grants-2015_03 |