HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 86726741, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-butyl N-[(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate | HCID 73977851 | — |
| Reactant | 4-Chloro-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine | HCID 86726686 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 86726741 | HCID 86726741 | 62.1% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
To a mixture of 4-chloro-3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridine (144.2 mg, 0.7260 mmol) and tert-butyl [(3S,5R)-5-(trifluoromethyl)piperidin-3-yl]carbamate (from MolBridge, 179.9 mg, 0.6706 mmol) was added 1-butanol (3.0 mL) followed by DIPEA (493.7 mg, 3.820 mmol). The mixture was stirred at 150° C. for 6 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-50% EtOAc in hexanes) to afford the sub-title compound as a pale yellow solid (179.2 mg, 62%). LCMS calc. for C19H26F3N4O4 (M+H)+: m/z=431.2. found 431.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09200004B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-8d21cb0a387046e7a55da60f3e605e81 |
| Source note | uspto-grants-2015_12 |