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

HRID 535841Notes

Reaction equation

HRID 535841 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.[Cl:14][C:15]1[CH:41]=[CH:40][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[C:24]([C:36]([F:39])([F:38])[F:37])[CH:23]=2)=[O:20])=[CH:17][C:16]=1I>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[C:24]([C:36]([F:38])([F:37])[F:39])[CH:23]=2)=[O:20])=[CH:40][C:41]=1[C:13]#[C:12][C:9]1[N:8]=[N:7][C:6]([NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 715626354-chloro-3-iodo-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamideHCID 86709554N-Cyclobutyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729499124-Chloro-3-(2-(6-(cyclobutylamino)pyridazin-3-yl)ethynyl)-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 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: 132-133° C.; 1H NMR (300 MHz, CDCl3) δ: 9.53 (1H, s), 8.10 (1H, s), 8.00 (2H, m), 7.85-7.87 (1H, d, J=6.0 Hz), 7.66-7.69 (1H, d, J=9.0 Hz), 7.43-7.45 (1H, d, J=6.0 Hz), 7.33-7.36 (1H, d, J=9.0 Hz), 6.58-6.61 (1H, d, J=9.0 Hz), 5.56 (1H, s), 4.23-4.25 (1H, m), 3.64 (2H, s), 2.61 (8H, brs), 2.44 (3H, s), 2.43 (2H, m), 1.91-1.97 (2H, m), 1.81-1.86 (1H, brs). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C30H31ClF3N6O: 583.2194. found: 583.2174.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-e0b6be4abe4942598b5af17a10693b99
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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