Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 4-(2-Fluoro-4-methoxyphenoxy)piperidine hydrochloride | HCID 118159158 | — |
| Reactant | 6-benzyl-3-chloro-N-cyclobutyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt | HCID 131734018 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 412.8% |
| Product | 6-benzyl-N-cyclobutyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine | HCID 118159209 | — |
Reaction Steps
A mixture of 4-(2-fluoro-4-methoxyphenoxy)piperidine hydrochloride (56.7 mg, 0.217 mmol), 6-benzyl-3-chloro-N-cyclobutyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (80 mg, 0.181 mmol), sodium tert-butoxide (52.1 mg, 0.542 mmol), BINAP (16.9 mg, 0.027 mmol) and Pd2(dba)3 (24.8 mg, 0.027 mmol) in toluene (602 μL) was heated at 90° C. in a sealed tube for 16 h. The mixture was purified by HPLC Method A to afford 6-benzyl-N-cyclobutyl-3-(4-(2-fluoro-4-methoxyphenoxy)piperidin-1-yl)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine as its TFA salt (85.2 mg, 74.7%) as a yellow foam. ESI-MS m/z [M+H]+ 518.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09181249B2 |
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| Source dataset | uspto-grants-2015_11 |
|---|
| ORD ID | ord-da28295a94914ea6a2c95f79b06c02bf |
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| Source note | uspto-grants-2015_11 |
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