Reaction equation
Cl[C:2]1[N:20]=[C:5]2[C:6]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH2:21]([N:23]1[CH:27]=[C:26]([NH2:28])[CH:25]=[N:24]1)[CH3:22].C1(P(C2CCCCC2)C2(P(C3CCCCC3)C3CCCCC3)CC=CC=C2C2C=CC=CC=2)CCCCC1>>[CH2:21]([N:23]1[CH:27]=[C:26]([NH:28][C:2]2[N:20]=[C:5]3[C:6]([C:10]4[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=4)=[CH:7][CH:8]=[CH:9][N:4]3[N:3]=2)[CH:25]=[N:24]1)[CH3:22]Participants
4
Reactant 3
Product 1
Procedure
(1-Ethyl-1H-pyrazol-4-yl)-[8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine was prepared from 2-chloro-8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1.5-a]pyridine (0.125 g, 0.406 mmol) and 1-ethyl-1H-pyrazol-4-ylamine (0.058 g, 0.52 mmol) with 2,2-bis-dicyclohexylphosphanyl-biphenyl (0.048 g, 0.088 mmol) as the ligand in a manner analogous to Example 2d. Product was isolated as a tan solid (0.09 g, 58%). MP=201-203° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.37 (s, 1H), 8.78 (d, J=6.48 Hz, 1H), 8.42 (d, J=8.05 Hz, 2H), 8.06 (d, J=8.09 Hz, 2H), 7.94 (d, J=7.21 Hz, 1H), 7.82 (s, 1H), 7.48 (s, 1H), 7.12 (t, J=7.08 Hz, 2H), 4.10 (q, J=7.08 Hz, 2H), 3.29 (s, 3H), 1.37 (t, J=7.16 Hz, 3H). MS=383 (MH)+.
Sources & evidence
- ORD record
- ord-3d0753fbe5d64c5f91174e91cdd037d0
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Linked notes
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