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

HRID 706828Notes

Reaction equation

HRID 706828 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].[Cl:13][C:14]1[CH:40]=[CH:39][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:23]([C:35]([F:38])([F:37])[F:36])[CH:22]=2)=[O:19])=[CH:16][C:15]=1I>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][N:28]3[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]3)=[C:23]([C:35]([F:37])([F:36])[F:38])[CH:22]=2)=[O:19])=[CH:39][C:40]=1[C:12]#[C:11][C:8]1[N:7]=[N:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 715626354-chloro-3-iodo-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamideHCID 86709557N-isopropyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729499134-Chloro-3-(2-(6-(isopropylamino)pyridazin-3-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from N-isopropyl-6-ethynylpyridazin-3-amine and 4-chloro-3-iodo-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:133-134° C.; 1H NMR (300 MHz, CDCl3) δ: 9.62 (1 H, s), 8.11 (1 H, s), 8.05 (1 H, s), 8.01-8.03 (1 H, d, J=9.0 Hz), 7.86-7.88 (1 H, d, J=6.0 Hz), 7.60-7.63 (1 H, d, J=6.0 Hz), 7.44-7.47 (1 H, d, J=9.0 Hz), 7.33-7.36 (1 H, d, J=9.0 Hz), 6.63-6.66 (1 H, d, J=9.0 Hz), 3.99-4.07 (1 H, m), 3.67 (2 H, s), 2.84 (8 H, brs), 2.56 (3 H, s), 1.25-1.30 (6 H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C29H30ClF3N6O: 571.2194. found: 571.2209.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-03b7cbbac43c4812881223d9d0e388f8
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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