Pyridine → N-(5-(3-bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide

HRID 539743Notes

Reaction equation

HRID 539743 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:20])=[C:17]([CH:19]=1)[NH2:18].N1C=CC=CC=1.[CH3:27][C:28]([CH3:33])([CH3:32])[C:29](Cl)=[O:30]>C(#N)C>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]2=[N:4][C:3]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:20])=[C:17]([NH:18][C:29](=[O:30])[C:28]([CH3:33])([CH3:32])[CH3:27])[CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 575162685-(3-Bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Product 1

HCID 68089171N-(5-(3-bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamideYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(3-bromo-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline (0.165 g, 0.495 mmol) in acetonitrile (25 mL) containing pyridine (1.48 mmol) is added trimethylacetylchloride (0.495 mmol). The mixture is stirred at room temperature for 4 hours, then concentrated to dryness and purified via chromatography (hexanes to EtOAc) to afford 0.200 g (97%) of the title compound as a white solid: Rf 0.41 (1:1 EtOAc:hexanes); LCMS (m/z)=417.3, 419.3 [M+H]+, tR=2.76 min.

Workup

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

Sources & evidence

ORD record
ord-cf7987ece76c4d57a18b5bc1d8e73e45
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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