HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → (5R,6S,8S)-5-Methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-Butyl[(5R,6S,8S)-5-methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate | HCID 131733072 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (5R,6S,8S)-5-Methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-amine | HCID 118185005 | 74% |
Reaction Steps
To a solution of tert-butyl[(5R,6S,8S)-5-methyl-6-phenyl-3-(2,2,2-trifluoroethyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-8-yl]carbamate (18.4 mg, 0.045 mmol) in dichloromethane (900 μL) was added trifluoroacetic acid (104 μL, 1.35 mmol). The mixture was stirred 90 min. N,N-dimethylformamide was added and the dichloromethane was removed under vacuum. The resulting mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid). Product containing fractions were treated with 1 M hydrochloric acid and concentrated to give the hydrochloride salt of the title compound (10.3 mg). MS 310.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09067941B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-3987be7261d04378abdb5a24a1b60759 |
| Source note | uspto-grants-2015_06 |