2-Amino-3-methylpyridine → HCID 68488194, compound

HRID 1725536Notes

Reaction equation

HRID 1725536 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[N+:19]([O-])=O)(=[O:3])[CH3:2].N[C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][N:24]=1>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][N:7]([CH2:16][CH3:17])[C:6](=[O:18])[C:5]=1[NH:19][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][N:24]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 68488194HCID 68488194, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 80 mg (0.278 mmol) of 5-acetyl-2-ethyl-4-nitro-6-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 2-amino-3-methylpyridine (45 mg, 0.417 mmol) was added portionwise. The resulting mixture was stirred at room temperature for five days. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 2:1) to yield the title compound (26 mg, 27% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by column chromatography (silica gel, hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-1909a196f15d413494b47934c3cb4a5b
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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