3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide → 3-(2-(6-(Isopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
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]([CH:36]=[CH:37][C:38]=1[CH3:39])[C:17]([NH:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)[CH:21]=1)=[O:18]>>[CH:1]([NH:4][C:5]1[N:6]=[N:7][C:8]([C:11]#[C:12][C:14]2[CH:15]=[C:16]([CH:36]=[CH:37][C:38]=2[CH3:39])[C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]([F:28])([F:27])[F:29])[CH:23]=[C:22]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)[CH:21]=2)=[O:18])=[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 3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp:192-194° C.; 1H NMR (300 MHz, DMSO-d6) δ: 10.73 (1 H, s), 8.33 (1 H, s), 8.17-8.22 (2 H, m), 7.94-7.96 (1 H, d, J=7.2 Hz), 7.76 (1 H, s), 7.54-7.57 (1 H, d, J=7.8 Hz), 7.45-7.48 (1 H, d, J=8.4 Hz), 7.15-7.18 (1 H, d, J=7.5 Hz), 6.79-6.82 (1 H, d, J=9.0 Hz), 4.14-4.20 (1 H, m), 2.56 (3 H, s), 2.19 (3 H, brs), 1.20-1.22 (6 H, d, J=6.3 Hz). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C28H26F3N6O: 519.2115. found: 519.2121.
Workup
- customThe product was obtained as a pale yellow solid
Sources & evidence
- ORD record
- ord-313fe4c2499c4cf3a135631bd4d4f68f
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174996B2
Reaction notes
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