2-Hydrazinopyridine → 1-(3-Difluoromethoxy-phenyl)-3-(2-pyridin-2-yl-2H-pyrazol-3-yl)-1H-pyridazin-4-one

HRID 1924568Notes

Reaction equation

HRID 1924568 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17](=O)/[CH:18]=[CH:19]/[N:20](C)C)=[N:11]2)[CH:7]=[CH:8][CH:9]=1.[NH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)N>C(O)C.Cl>[F:1][CH:2]([F:24])[O:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[C:12]([C:17]3[N:25]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[N:20]=[CH:19][CH:18]=3)=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 786452-HydrazinopyridineHCID 593700141-(3-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one

Product 1

HCID 462201451-(3-Difluoromethoxy-phenyl)-3-(2-pyridin-2-yl-2H-pyrazol-3-yl)-1H-pyridazin-4-oneYield 40.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

1-(3-Difluoromethoxy-phenyl)-3-((E)-3-dimethylamino-acryloyl)-1H-pyridazin-4-one (A-10) (0.05 g; 0.149 mmol) and 2-hydrazinopyridine (0.021 g; 0.194 mmol) are dissolved in a sealed tube in ethanol (0.6 ml) with catalytic amounts of HCl and irradiated at 160° C. for 5 min. The solvent of the reaction mixture is removed and the crude product is purified by preparative HPLC yielding 0.023 g (40.5%) of the final product. MS: M=382.2 (M+H)+

Workup

  1. customirradiated at 160° C. for 5 min
  2. customThe solvent of the reaction mixture is removed
  3. customthe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-23d13a5775334a8d96edf3f1d3606702
Source dataset
uspto-grants-2012_05
Patent number
US08178538B2

Reaction notes

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