3-(4-Methylpiperazin-1-yl)aniline → HCID 59612602, compound

HRID 1890034Notes

Reaction equation

HRID 1890034 reaction equation
Cl[C:2]1[N:22]=[C:5]2[C:6]([C:10]3[CH:11]=[N:12][N:13]([C:15]4[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=4)[CH:14]=3)=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=2)[NH2:33])[CH2:26][CH2:25]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([N:13]2[CH:14]=[C:10]([C:6]3[C:5]4[N:4]([N:3]=[C:2]([NH:33][C:32]5[CH:34]=[CH:35][CH:36]=[C:30]([N:27]6[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]6)[CH:31]=5)[N:22]=4)[CH:9]=[CH:8][CH:7]=3)[CH:11]=[N:12]2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67481411HCID 67481411, compound

Product 1

HCID 59612602HCID 59612602, compound

Procedure

{8-[1-(4-Fluoro-phenyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine-2-yl}-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine was prepared from 2-chloro-8-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine (Example 280a) and 3-(4-methylpiperazine-1-yl)aniline with 2,2′-bis-dicyclohexylphosphanyl-biphenyl as the ligand in a manner analogous to Example 2d (0.055 g, 20%). MP=216-218° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.53 (s, 1H), 9.25 (s, 1H), 8.67 (d, 2H), 7.92 (m, 3H), 7.43 (m, 3H), 7.12 (m, 3H), 6.50 (m, 1H), 3.12 (m, 4H), 2.43 (m, 4H), 2.21 (s, 3H). MS=469 (MH)+.

Sources & evidence

ORD record
ord-91f91dd8cf1041f1909d892832fcf16c
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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