Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | (5-Chloro-2-fluorophenyl)(piperidin-4-YL)methanone hydrochloride | HCID 49761186 | — |
| Reactant | 6-benzyl-3-chloro-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt | HCID 131734007 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Trifluoroacetic acid | HCID 6422 | 205.2% |
| Product | (1-(6-Benzyl-2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone | HCID 118159404 | — |
Reaction Steps
A mixture of (5-chloro-2-fluorophenyl)(piperidin-4-yl)methanone hydrochloride (69.7 mg, 0.251 mmol), 6-benzyl-3-chloro-N-isopropyl-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-2-amine TFA salt (90 mg, 0.209 mmol), sodium tert-butoxide (60.2 mg, 0.627 mmol), BINAP (19.5 mg, 0.031 mmol) and Pd2(dba)3 (9.6 mg, 10.4 μmol) in toluene (1.04 mL) was heated at 100° C. for 16 h. The mixture was purified by HPLC Method A to afford (1-(6-benzyl-2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-b]pyrazin-3-yl)piperidin-4-yl)(5-chloro-2-fluorophenyl)methanone as its TFA salt (48.9 mg, 36.8%) as a yellow oil. ESI-MS m/z [M+H]+ 523.4.
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-d6d9222e0e33461fb6c929681724d035 |
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| Source note | uspto-grants-2015_11 |
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