HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile → 4-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-ethyl)-benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile | HCID 67324068 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-(2-{5-[6-(4-Methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-ethyl)-benzonitrile | HCID 67325770 | 44.4% |
Reaction Steps
A mixture of the 4-(2-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-vinyl)-benzonitrile (72 mg, 0.189 mmol) and 10% palladium on activated carbon (27 mg) in MeOH and DCM (10 ml each) was stirred vigorously under an atmosphere of hydrogen at ambient temperature and pressure for 24 h. Further catalyst (27 mg) was added and the mixture stirred for a further 18 h. The mixture was filtered and evaporated under reduced pressure before trituration from DCM/pentane to afford the title compound as a pale yellow solid (32 mg, 44%). 1H NMR (300 MHz, DMSO-d6) δ 9.75 (s, 1H), 8.10 (d, J=5.0 Hz, 1H), 7.89-7.39 (m, 8H), 7.17 (d, J=7.2 Hz, 1H), 6.73 (t, J=13.6 Hz, 1H), 3.22 (s, 4H), 2.31 (s, 3H). (ESI+) m/z 382 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08962665B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-0e9c02113f064d869a8398e86e58e49f |
| Source note | uspto-grants-2015_02 |