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
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[O:19][C:18]([CH:20]=[CH:21][C:22]4[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1>[Pd].CO.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[O:19][C:18]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=4)=[N:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=2)[CH:3]=1Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Procedure
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).
Workup
- stirringthe mixture stirred for a further 18 h
- filtrationThe mixture was filtered
- customevaporated under reduced pressure before trituration from DCM/pentane
Sources & evidence
- ORD record
- ord-0e9c02113f064d869a8398e86e58e49f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962665B2
Reaction notes
Loading…