Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Cyano-2-fluorobenzoic acid | HCID 590659 | — |
| Reactant | (R)-1-Boc-3-methylpiperazine | HCID 2756811 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58180914 | HCID 58180914 | — |
Reaction Steps
Triethylamine (803 μL, 5.76 mmol) was added to a mixture of 4-cyano-2-fluorobenzoic acid (247 mg, 1.50 mmol, Alfa Aesar) and N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (522 mg, 1.37 mmol) in THF (11 mL). After stirring for 15 min, tert-butyl (3R)-3-methylpiperazine-1-carboxylate (0.25 g, 1.2 mmol, Aldrich) was added. The mixture was stirred for 3 h. Ethyl acetate and water were added, shaken and the layers separated. The organic layer was washed with water, 0.1N NaOH, and brine; dried over sodium sulfate, decanted and concentrated to afford product which was used without further purification (450 mg, 100%). 1H NMR (400 MHz, CDCl3, rotamers): δ 7.57-7.40 (m, 3H), 4.98-2.63 (m, 7H), 1.47 (s, 9H), 1.28 (d, 1.8H), 1.19 (br s, 1.2H); LCMS (M-tBu+2H)+: 292.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09249145B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-63787c0921e547578a27e5e2379c4dfa |
|---|
| Source note | uspto-grants-2016_02 |
|---|
