Potassium Carbonate → N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamide

HRID 2391206Notes

Reaction equation

HRID 2391206 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].CC(C)([O-])C.[K+].I[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[C:24]([NH:26][C:27]([CH:29]3[CH2:31][CH:30]3[CH3:32])=[O:28])[N:25]=2)[N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[CH3:8])[O:9][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([CH:23]=[C:24]([NH:26][C:27]([CH:29]3[CH2:31][CH:30]3[CH3:32])=[O:28])[N:25]=2)[N:22]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 178203-Amino-p-cresolHCID 23665647Potassium tert-butoxideHCID 57505473N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-2-methylcyclopropanecarboxamide

Product 1

HCID 57505472N-[6-(3-amino-4-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]-2-methylcyclopropanecarboxamideYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using 3-amino-4-methylphenol (1.08 g, 8.77 mmol), N,N-dimethylformamide (30.0 mL), potassium tert-butoxide (1.02 g, 9.13 mmol), N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)-2-methylcyclopropanecarboxamide (2.5 g, 7.31 mmol) and potassium carbonate (0.51 g, 3.65 mmol), and in the same manner as in Example 216, the title compound (1.38 g, 56%) was obtained as a brown powder.

Sources & evidence

ORD record
ord-ea52fa8524034a2baab9378d124ea13e
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

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