3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide → 3-(2-(6-(Cyclobutylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 535853Notes

Reaction equation

HRID 535853 reaction equation
[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1.I[C:15]1[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=1[CH3:40])[C:18]([NH:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([N:31]2[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]2)[CH:22]=1)=[O:19]>>[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[C:13][C:15]3[CH:16]=[C:17]([CH:37]=[CH:38][C:39]=3[CH3:40])[C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:29])([F:28])[F:30])[CH:24]=[C:23]([N:31]4[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]4)[CH:22]=3)=[O:19])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 177521583-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamideHCID 86709554N-Cyclobutyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729502513-(2-(6-(Cyclobutylamino)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-cyclobutyl-6-ethynylpyridazin-3-amine and 3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (as prepared above) in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp: 223-225° C.; 1H NMR (300 MHz, DMSO-d6) δ: 10.72 (1H, s), 8.31 (1H, s), 8.17-8.22 (2H, m), 7.94-7.96 (1H, dd, J=1.5 and 8.1 Hz), 7.75 (1H, s), 7.47-7.61 (4H, m), 6.77-6.80 (1H, d, J=9.0 Hz), 4.42 (1H, m), 2.56 (3H, s), 2.33-2.35 (2H, m), 2.19 (3H, brs), 1.88-1.99 (2H, m), 1.72-1.78 (2H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C29H26F3N6O: 531.2115. found: 531.2113.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-547abb4a1b134a80867ed6dcd341f978
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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