3-Ethynylimidazo[1,2-b]pyridazine → 4-Chloro-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 706844Notes

Reaction equation

HRID 706844 reaction equation
[C:1]([C:3]1[N:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=1)#[CH:2].[Cl:12][C:13]1[CH:37]=[CH:36][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)[CH:21]=2)=[O:18])=[CH:15][C:14]=1I>>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=[C:22]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)[CH:21]=2)=[O:18])=[CH:36][C:37]=1[C:2]#[C:1][C:3]1[N:7]2[N:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 468387603-Ethynylimidazo[1,2-b]pyridazineHCID 867095644-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729504184-Chloro-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from 3-ethynylimidazo[1,2-b]pyridazine and 4-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide in a manner similar to that described for in Example 1. The title compound was obtained as a light yellow solid. Mp: 153-154° C.; 1H NMR (300 MHz, CDCl3) δ: 9.35 (1 H, s), 8.48-8.49 (1 H, d, J=3.6 Hz), 8.25 (1 H, s), 8.15 (2 H, brs), 7.89-7.92 (4 H, m), 7.57-7.60 (1 H, d, J=8.4 Hz), 7.37 (1 H, s), 7.12-7.16 (1 H, dd, J=4.2 and 9.3 Hz), 2.27 (3 H, s). HRMS (ESI-TOF+): m/z [M+2H]+2 calcd for C26H18ClF3N6O: 261.0586. found: 261.0584.

Sources & evidence

ORD record
ord-90b72a84d0554f898475755b7abf0d1c
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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