1-(3-Bromophenyl)-4-methylpiperazine → 2-{2-[3-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl}benzonitrile
Reaction equation
[NH2:1][C:2]1[N:20]=[C:5]2[C:6]([O:10][CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.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>>[CH3:34][N:31]1[CH2:32][CH2:33][N:28]([C:24]2[CH:25]=[C:26]([NH:1][C:2]3[N:20]=[C:5]4[C:6]([O:10][CH2:11][C:12]5[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=5[C:14]#[N:15])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)[CH:27]=[CH:22][CH:23]=2)[CH2:29][CH2:30]1Participants
3
Procedure
2-{2-[3-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl}benzonitrile was prepared from 2-(2-amino-[1,2,4]triazolo[1,5-a]pyridin-8-yloxymethyl)-benzonitrile (115.0 mg, 0.434 mmol) and 1-(3-bromo-phenyl)-4-methyl-piperazine (128 mg, 0.500 mmol in a manner analogous to Example 2d. Product was isolated as a pale orange solid (0.111 g, 58%). MP=68-70° C. (foam). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.46 (s, 1H), 8.43 (d, J=6.4 Hz, 1H), 7.95 (d, J=7.9 Hz, 1H), 7.81-7.79 (m, 2H), 7.64-7.62 (m, 1H), 7.33 (s, 1H), 7.20 (d, J=7.2 Hz, 1H), 7.09 (d, J=4.8 Hz, 2H), 6.96-6.92 (m, 1H), 6.47-6.44 (m, 1H), 5.50 (s, 2H), 3.12-3.09 (m, 4H), 2.44-2.42 (m, 4H), 2.22 (s, 3H). MS=440 (MH)+.
Sources & evidence
- ORD record
- ord-224dd3f2939547c4aa21850a1c8cf464
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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