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

HRID 535854Notes

Reaction equation

HRID 535854 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

HCID 177521583-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamideHCID 86709557N-isopropyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729502523-(2-(6-(Isopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

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 (1H, s), 8.33 (1H, s), 8.17-8.22 (2H, m), 7.94-7.96 (1H, d, J=7.2 Hz), 7.76 (1H, s), 7.54-7.57 (1H, d, J=7.8 Hz), 7.45-7.48 (1H, d, J=8.4 Hz), 7.15-7.18 (1H, d, J=7.5 Hz), 6.79-6.82 (1H, d, J=9.0 Hz), 4.14-4.20 (1H, m), 2.56 (3H, s), 2.19 (3H, brs), 1.20-1.22 (6H, d, J=6.3 Hz). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C28H26F3N6O: 519.2115. found: 519.2121.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-a044b665085c45faaf44c805328f2663
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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