2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-meth anesulfonyloxymethyl-2H-pyridazin-3-one → 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methylaminomethyl-2H-pyridazin-3-one

HRID 7922Notes

Reaction equation

HRID 7922 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12]OS(C)(=O)=O)=[CH:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([F:26])[CH:19]=3)=[N:6]2)[CH2:3][CH2:2]1.[CH3:27][NH2:28].C(O)C>>[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][NH:28][CH3:27])=[CH:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([F:26])[CH:19]=3)=[N:6]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 219916182-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-meth anesulfonyloxymethyl-2H-pyridazin-3-oneHCID 22028356Methylamine ethanol

Product 1

HCID 219915182-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methylaminomethyl-2H-pyridazin-3-one

Procedure

A solution of 2-cyclopropylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one (160 mg, 0.42 mmol) in 30% methylamine/ethanol (5 mL) was stirred at 80° C. for 4 hours in a sealed tube. The solvent was distilled off under reduced pressure, and the residue was purified by preparative thin-layer chromatography on silica gel [developing solvent: chloroform/methanol (10/1)] to yield title compound as a slightly yellow oil (87 mg, 65.5%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by preparative thin-layer chromatography on silica gel [developing solvent: chloroform/methanol (10/1)]

Sources & evidence

ORD record
ord-b6888d75665f483bbf89bb734af68f01
Source dataset
uspto-grants-2006_08
Patent number
US07087606B2

Reaction notes

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