3-(2-(2-Methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)imidazo[1,2-b]pyridazine → 3-(2-(2-Chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)imidazo[1,2-b]pyridazine
Reaction equation
C[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([CH2:17][N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[N:31]2[N:32]=[CH:33][CH:34]=[CH:35][C:30]2=[N:29][CH:28]=1.[Cl:36]C1C=CC(C2NC3C=C(CN4CCN(C)CC4)C=CC=3N=2)=CC=1I>>[Cl:36][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[C:14]([CH2:17][N:18]4[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]4)[CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:4][C:3]=1[C:25]#[C:26][C:27]1[N:31]2[N:32]=[CH:33][CH:34]=[CH:35][C:30]2=[N:29][CH:28]=1Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized from 3-ethynylimidazo[1,2-b]pyridazine (as prepared in Example 3) and 2-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzoimidazole in a manner similar to that described for in Example 1. The intermediate compound 2-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole was made as for Example 1 (Step 4 to 7) with the spectra below: 1H NMR (300 MHz, CDCl3) δ: 8.52 (1 H, s), 7.95-7.98 (1 H, d, J=9.0 Hz), 7.45-7.48 (1 H, d, J=9.0 Hz), 7.43-7.46 (1 H, d, J=9.0 Hz), 7.23 (1 H, s), 7.21-7.24 (1 H, d, J=9.0 Hz), 3.59 (2 H, s), 2.51 (8H, brs), 2.29 (3 H, s).
Sources & evidence
- ORD record
- ord-662b4a3972a7487e9f8e345ee475a360
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174996B2
Reaction notes
Loading…