HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 59149753, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Chloro-3-(trifluoromethyl)-(1,2,4)triazolo(4,3-b)pyridazine | HCID 613657 | — |
| Reactant | (2S,5R)-1-Benzyl-2,5-dimethylpiperazine | HCID 23402345 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59149753 | HCID 59149753 | 79% |
Reaction Steps
A stirred solution of 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazine (4.45 g, 20 mmol), (2S,5R)-1-benzyl-2,5-dimethylpiperazine (4.90 g, 24.00 mmol) and DIPEA (5.14 mL, 30.00 mmol) in DMF (40 mL) was heated at 125° C. for 2 hours. The reaction mixture was evaporated to dryness, redissolved in DCM and washed sequentially with 1M aqueous K2CO3, water and saturated brine. The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by MPLC silica chromatography, eluting with 75% EtOAc/isohexane. Pure fractions were evaporated to dryness to afford 6-[(2R,5S)-4-benzyl-2,5-dimethylpiperazin-1-yl]-3-(trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazine (6.16 g, 79%) as a tan gum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08003649B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-d06c921039b64d7a9b9730f4b6ed5f94 |
| Source note | uspto-grants-2011_08 |