3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide → 3-(2-(6-(Cyclobutylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

HRID 535838Notes

Reaction equation

HRID 535838 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:39]=[CH:40][C:41]=1[CH3:42])[C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)=[C:23]([C:35]([F:38])([F:37])[F:36])[CH:22]=1)=[O:19]>>[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[C:13][C:40]3[CH:39]=[C:17]([CH:16]=[CH:15][C:41]=3[CH3:42])[C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)=[C:23]([C:35]([F:38])([F:37])[F:36])[CH:22]=3)=[O:19])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 468389103-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamideHCID 86709554N-Cyclobutyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729497353-(2-(6-(Cyclobutylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from N-cyclobutyl-6-ethynylpyridazin-3-amine and 3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp: 120-121° C.; 1H NMR (300 MHz, CDCl3) δ: 9.10 (1H, s), 8.05 (1H, s), 7.97-7.80 (1H, d, J=9.0 Hz), 7.94 (1H, s), 7.81-7.83 (1H, d, J=6.0 Hz), 7.64-7.66 (1H, d, J=6.0 Hz), 7.28-7.31 (1H, d, J=9.0 Hz), 7.26-7.28 (1H, d, J=6.0 Hz), 6.57-5.59 (1H, d, J=2.0 Hz), 5.53 (1H, s), 4.22-4.27 (1H, m), 3.64 (2H, s), 2.65 (8H, brs), 2.49 (3H, s), 2.45 (3H, s), 2.44 (2H, m), 1.93-1.99 (2H, m), 1.83-1.89 (2H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C31H34F3N6O: 563.2741. found: 563.2768.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-aafd7738f1f64f2baec5f13fb87f2467
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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