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

HRID 706843Notes

Reaction equation

HRID 706843 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]=[CH:24][C:23]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:22]([C:32]([F:35])([F:34])[F:33])[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]=[CH:24][C:23]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:22]([C:32]([F:34])([F:33])[F:35])[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 867095634-chloro-3-iodo-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729504174-Chloro-3-(2-(imidazo[1,2-b]pyridazin-3-yl)ethynyl)-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from 3-ethynylimidazo[1,2-b]pyridazine and 4-chloro-3-iodo-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(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: 153-155° C.; 1H NMR (300 MHz, CDCl3) δ: 9.39 (1 H, s), 8.49 (1 H, d, J=3.3 Hz), 8.08-8.18 (4 H, m), 7.91-7.94 (2 H, m), 7.57-7.60 (2 H, m), 7.34 (1 H, brs), 7.14-7.16 (1 H, m), 6.85 (1 H, brs), 2.28 (3 H, s). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C26H17ClF3N6O: 521.1099. found: 521.1092.

Sources & evidence

ORD record
ord-f664e1ce74d34e06b8ce1cef56bac39e
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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