5-Aminoisoquinoline → 5-Acetyl-6-(3-chlorophenyl)-2-ethyl-4-(isoquinolin-5-ylamino)pyridazin-3(2H)-one

HRID 1725548Notes

Reaction equation

HRID 1725548 reaction equation
[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[N:8][N:7]([CH2:17][CH3:18])[C:6](=[O:19])[C:5]=1[N+:20]([O-])=O)(=[O:3])[CH3:2].N[C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][N:28]=[CH:29]2>C(O)C>[C:1]([C:4]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)=[N:8][N:7]([CH2:17][CH3:18])[C:6](=[O:19])[C:5]=1[NH:20][C:24]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:25]=1[CH:26]=[CH:27][N:28]=[CH:29]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 707665-AminoisoquinolineHCID 105198325-acetyl-2-ethyl-4-nitro-6-(3-chlorophenyl)pyridazin-3(2H)-one

Product 1

HCID 684833055-Acetyl-6-(3-chlorophenyl)-2-ethyl-4-(isoquinolin-5-ylamino)pyridazin-3(2H)-oneYield 21.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 100 mg (0.311 mmol) of 5-acetyl-2-ethyl-4-nitro-6-(3-chlorophenyl)pyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in ethanol (4 mL), 5-amino-isoquinoline (67 mg, 0.467 mmol) was added. The resulting mixture was stirred at room temperature for two hours. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 1:2) to yield the title compound (28 mg, 21.5% yield).

Workup

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

Sources & evidence

ORD record
ord-8df9e082094a4369b84a1ae61eb03328
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

Loading…