Hydrochloric Acid → [8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(1-methyl-piperidin-4-yl)-phenyl]-amine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:23]=[C:24]([CH:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1.Cl.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:26]4[CH:27]=[CH:22][CH:23]=[C:24]([CH:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)[CH:25]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]Participants
Reactant 4
Product 1
Procedure
[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(1-methyl-piperidin-4-yl)-phenyl]-amine was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 4-(3-bromo-phenyl)-1-methyl-piperidine; hydrochloride (90.0 mg, 0.310 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (30.0 mg, 0.0549 mmol) as the ligand in a manner analogous to Step 2d. The title compound was isolated as a tan solid (0.031 g, 26%). MP=208-210° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.5 Hz, 1H), 8.08 (d, J=8.3 Hz, 2H), 8.10 (d, J=7.3 Hz, 2H), 7.66 (d, J=6.6 Hz, 1H), 7.55 (s, 1H), 7.38 (d, J=8.7 Hz, 1H), 7.31-7.25 (m, 1H), 7.02 (t, J=7.4 Hz, 1H), 6.91-6.85 (m, 2H), 3.10 (s, 3H), 3.01 (d, J=10.9 Hz, 2H), 2.57-2.45 (m, 1H), 2.35 (S, 3H), 2.11-2.03 (m, 2H), 1.92-1.83 (m, 4H). MS=462 (MH)+.
Sources & evidence
- ORD record
- ord-3e9f94df81b940e9926b9d60aacda7d2
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
Loading…