Pyridine → N-(5-(6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide

HRID 539733Notes

Reaction equation

HRID 539733 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([CH:18]=3)[NH2:17])[N:11]=2)[N:8]=1.N1C=CC=CC=1.[CH3:26][C:27]([CH3:32])([CH3:31])[C:28](Cl)=[O:29]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([CH3:19])=[C:16]([NH:17][C:28](=[O:29])[C:27]([CH3:32])([CH3:31])[CH3:26])[CH:18]=3)[N:11]=2)[N:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 529038205-(6-Methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Product 1

HCID 16885922N-(5-(6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamideYield 86.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 5-(6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline (0.050 g, 0.206 mmol) in acetonitrile (5 mL) containing pyridine (0.618 mmol) is added trimethylacetylchloride (0.206 mmol). The mixture is stirred at room temperature for 4 hours, concentrated to dryness, then purified via chromatography (hexanes to EtOAc) to afford the title compound (0.060 g, 86%) as a white solid: Rf 0.57 (EtOAc); LCMS (m/z)=339.4 [M+H]+, tR=6.37 min. (10 min run)

Workup

  1. concentrationconcentrated to dryness
  2. custompurified via chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-9ca5699501554ce9a11f8ba48984248d
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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