HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → (S)-2-Bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-Phenylbutan-2-amine, (S)- | HCID 6994564 | — |
| Reactant | 2,4-Dibromopyridine-3-carbonitrile | HCID 57459591 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (S)-2-Bromo-4-((4-phenylbutan-2-yl)amino)nicotinonitrile | HCID 86696509 | 60.2% |
Reaction Steps
Prepared according to the methods above using 2,4-dibromonicotinonitrile (100 mg, 0.382 mmol), (S)-1-Methyl-3-phenyl-propylamine (58.1 mg, 0.382 mmol) and Hunig's Base (0.080 mL, 0.458 mmol) in DMF (1.5 mL) at 120° C. for 30 min to give the desired product as a clear oil (76 mg). LC/MS (316/318, [M−H]/[M+H]+); 1H NMR (400 MHz, CHLOROFORM-d) δ 8.05 (d, J=5.5 Hz, 1H), 7.33-7.25 (m, 2H), 7.23-7.15 (m, 3H), 6.81 (d, J=5.3 Hz, 1H), 5.06 (br. s., 1H), 4.33 (dt, J=14.0, 6.9 Hz, 1H), 2.71 (t, J=8.0 Hz, 2H), 1.98-1.83 (m, 2H), 1.32-1.25 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765767B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-76ab4146273f458ba26152e2db572a76 |
| Source note | uspto-grants-2014_07 |