1-(3-Bromophenyl)-4-methylpiperazine → [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([N:28]5[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]5)[CH:23]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]Participants
Procedure
[5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75 mg, 0.26 mmol) and 1-(3-bromo-phenyl)-4-methyl-piperazine (73 mg, 0.29 mmol) in a manner analogous to Example 77 to yield [5-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine (52 mg, 43%) as a yellow powder following purification on a 12 g Isco silica gel column using methanol in dichloromethane (0-10%) as eluent. MP=251° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.52 (s, 1H), 8.33 (d, J=8.6 Hz, 2H), 8.12 (d, J=8.6 Hz, 2H), 7.61-7.72 (m, 2H), 7.53 (s, 1H), 7.26 (d, J=7.5 Hz, 1H), 7.07 (t, J=15.0 Hz, 8.6 Hz, 1H), 6.86 (d, J=7.5 Hz, 1H), 6.45 (d, J=7.5 Hz, 1H), 3.33 (s, 3H), 3.04 (s, 4H), 2.44 (s, 4H), 2.22 (s, 3H). MS=463 (MH)+.
Sources & evidence
- ORD record
- ord-7c279925f4d9456bb1604808f10f0078
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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