3-Ethynylimidazo[1,2-b]pyridazine → HCID 178429870, compound

HRID 706819Notes

Reaction equation

HRID 706819 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]([C:20]2[NH:24][C:23]3[CH:25]=[C:26]([N:29]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]4)[CH:27]=[CH:28][C:22]=3[N:21]=2)[CH:16]=[CH:17][C:18]=1[CH3:19]>>[CH3:19][C:18]1[CH:17]=[CH:16][C:15]([C:20]2[NH:21][C:22]3[CH:28]=[CH:27][C:26]([N:29]4[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]4)=[CH:25][C:23]=3[N:24]=2)=[CH:14][C:13]=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 867095612-(3-Iodo-4-methylphenyl)-6-(4-methyl-1H-imidazol-1-yl)-1H-benzo[d]imidazole

Product 1

HCID 178429870HCID 178429870, compound

Procedure

The title compound was synthesized from 3-ethynylimidazo[1,2-b]pyridazine and 2-(3-iodo-4-methylphenyl)-6-(4-methyl-1H-imidazol-1-yl)-1H-benzo[d]imidazole (as prepared above) in a manner similar to that described for in Example 1. The title compound was obtained a pale yellow solid. Mp: 182-184° C.; 1H NMR (400 MHz, CD3OD) δ: 8.57 (2 H, brs), 8.26 (1 H, s), 7.98-8.05 (3 H, m), 7.74 (1 H, s), 7.68-7.70 (1 H, d, J=8.4 Hz), 7.46-7.48 (2 H, m), 7.42-7.44 (1 H, d, J=8.4 Hz), 7.29-7.33 (1 H, dd, J=4.4 and 9.2 Hz), 2.61 (3 H, s), 2.31 (3 H, s). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C26H20N7: 430.1775. found: 430.1778.

Sources & evidence

ORD record
ord-6b36ac941ad74c89a447675c01443a12
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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