2-(3-Iodo-4-methylphenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole → N-Isopropyl-6-(2-(2-methyl-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)pyridazin-3-amine
Reaction equation
[CH:1]([NH:4][C:5]1[N:6]=[N:7][C:8]([C:11]#[CH:12])=[CH:9][CH:10]=1)([CH3:3])[CH3:2].I[C:14]1[CH:15]=[C:16]([C:21]2[NH:25][C:24]3[CH:26]=[C:27]([CH2:30][N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[CH:28]=[CH:29][C:23]=3[N:22]=2)[CH:17]=[CH:18][C:19]=1[CH3:20]>>[CH:1]([NH:4][C:5]1[N:6]=[N:7][C:8]([C:11]#[C:12][C:14]2[CH:15]=[C:16]([C:21]3[NH:25][C:24]4[CH:26]=[C:27]([CH2:30][N:31]5[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]5)[CH:28]=[CH:29][C:23]=4[N:22]=3)[CH:17]=[CH:18][C:19]=2[CH3:20])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized from N-isopropyl-6-ethynylpyridazin-3-amine and 2-(3-iodo-4-methylphenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]-imidazole (as prepared in Example 1) in a manner similar to that described for in Example 1. The intermediate compound N-isopropyl-6-ethynylpyridazin-3-amine was made as for Example 1 (Step 1 to 3) with the spectra below: 1H NMR (300 MHz, CDCl3) δ: 7.26-7.29 (1 H, d, J=9.0 Hz), 6.54-6.57 (1 H, d, J=9.0 Hz), 5.00 (1 H, s), 3.97-4.04 (1 H, m), 3.25 (1 H, s), 1.29 (3 H, s), 1.27 (3 H, s).
Sources & evidence
- ORD record
- ord-fd5e345aacb543e0bac6f4e01277f326
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174996B2
Reaction notes
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