Pyridine → N-(5-(3-(4-fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamide

HRID 539741Notes

Reaction equation

HRID 539741 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([CH:25]=2)[NH2:24])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:33][C:34]([CH3:39])([CH3:38])[C:35](Cl)=[O:36]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[N:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:19]2[CH:20]=[CH:21][C:22]([CH3:26])=[C:23]([NH:24][C:35](=[O:36])[C:34]([CH3:39])([CH3:38])[CH3:33])[CH:25]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 680890985-(3-(4-Fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline

Product 1

HCID 57406705N-(5-(3-(4-fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylphenyl)pivalamideYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-(3-(4-fluorophenyl)-6-methoxyimidazo[1,2-b]pyridazin-2-yl)-2-methylaniline (0.025 g, 0.072 mmol) in acetonitrile (1 mL) containing pyridine (0.215 mmol) is added trimethylacetylchloride (0.072 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 (0.028 g, 90%) as a yellow solid: Rf 0.28 (1:1 EtOAc:hexanes); LCMS (m/z)=433.5 [M+H]+, tR=2.74 min. (compound same as Example 114)

Workup

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

Sources & evidence

ORD record
ord-e0ff701efd93451ea1205ce9af4f9b20
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

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