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

HRID 539737Notes

Reaction equation

HRID 539737 reaction equation
[Cl: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>[Cl: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 575162675-(3-Chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Product 1

HCID 57406704N-(5-(3-chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamideYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-(3-chloro-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline (0.025 g, 0.0867 mmol) in acetonitrile (1 mL) containing pyridine (0.261 mmol) is added trimethylacetylchloride (0.0867 mmol). The mixture is stirred at room temperature for 4 hours, then concentrated to dryness and purified via chromatography (hexanes to EtOAc) to afford the title compound (0.030 g, 93%) as a white solid: LCMS (m/z)=373.4, 375.3 [M+H]+, tR=2.74 min. (compound same as Example 109)

Workup

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

Sources & evidence

ORD record
ord-56314e44058a49309647068855266255
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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