4-Hydrazino-2-methylpyridine → 1-(3-Methanesulfonyl-phenyl)-3-[2-(2-methyl-pyridin-4-yl)-2H-pyrazol-3-yl]-1H-pyridazin-4-one

HRID 1924567Notes

Reaction equation

HRID 1924567 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]([C:7]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:15]=2)[N:8]=1)=O.[NH:25]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=1)N>CN(C)C=O>[CH3:23][S:20]([C:16]1[CH:15]=[C:14]([N:9]2[CH:10]=[CH:11][C:12](=[O:13])[C:7]([C:5]3[N:25]([C:27]4[CH:32]=[CH:31][N:30]=[C:29]([CH3:33])[CH:28]=4)[N:2]=[CH:3][CH:4]=3)=[N:8]2)[CH:19]=[CH:18][CH:17]=1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 200736634-Hydrazino-2-methylpyridineHCID 593701713-((E)-3-Dimethylamino-acryloyl)-1-(3-methansulfonyl-phenyl)-1H-pyridazin-4-one

Product 1

HCID 462190711-(3-Methanesulfonyl-phenyl)-3-[2-(2-methyl-pyridin-4-yl)-2H-pyrazol-3-yl]-1H-pyridazin-4-oneYield 34.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-((E)-3-Dimethylamino-acryloyl)-1-(3-methansulfonyl-phenyl)-1H-pyridazin-4-one (A-7) (0.05 g; 0.144 mmol) and 4-hydrazino-2-methylpyridine (0.03 g; 0.187 mmol) are dissolved in a sealed tube in dimethylformamide (0.6 ml) and irradiated at 180° C. for 10 min. The solvent of the reaction mixture is removed and the crude product is purified by preparative HPLC yielding 0.02 g (34.1%) of the final product. MS: M=408.4 (M+H)+

Workup

  1. customirradiated at 180° C. for 10 min
  2. customThe solvent of the reaction mixture is removed
  3. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-60cbac195fbb485c84f9ae8152d1cc62
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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