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

HRID 535857Notes

Reaction equation

HRID 535857 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].I[C:13]1[CH:14]=[C:15]([CH:35]=[CH:36][C:37]=1[CH3:38])[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]2)=[C:21]([C:31]([F:34])([F:33])[F:32])[CH:20]=1)=[O:17]>>[N:5]1[CH:4]=[C:3]([C:1]#[C:2][C:36]2[CH:35]=[C:15]([CH:14]=[CH:13][C:37]=2[CH3:38])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([C:31]([F:32])([F:33])[F:34])[CH:20]=2)=[O:17])[N:7]2[C:6]=1[CH:11]=[CH:10][CH:9]=[N:8]2

Participants

3

Reactant 2

HCID 468387603-Ethynylimidazo[1,2-b]pyridazineHCID 867095623-iodo-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-3(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729504163-(2-(Imidazo[1,2-b]pyridazin-3-yl)ethynyl)-4-methyl-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 3-iodo-4-methyl-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: 124-126° C.; 1H NMR (300 MHz, CDCl3) δ: 9.00 (1H, s), 8.48 (1H, d, J=4.8 Hz), 8.17 (1H, s), 8.09 (3H, m), 7.93-7.95 (1H, d, J=8.7 Hz), 7.86-7.89 (1H, d, J=8.1 Hz), 7.55 (1H, s), 7.39-7.42 (1H, d, J=8.1 Hz), 7.34-7.36 (1H, d, J=8.4 Hz), 7.11-7.16 (1H, dd, J=4.2 and 8.4 Hz), 6.82 (1H, s), 2.64 (3H, s), 2.29 (3H, s). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C27H20F3N6O: 501.1645. found: 501.1626.

Sources & evidence

ORD record
ord-ada2263ad6b44b0cac63fc020e9eab7c
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

Loading…