Ethanol → HCID 67109556, compound

HRID 1725530Notes

Reaction equation

HRID 1725530 reaction equation
C(C1C([N+]([O-])=O)=CC(CC)=[C:8]([N:10]2[C:15](=[O:16])[CH:14]=[CH:13][CH:12]=[N:11]2)[CH:9]=1)(=O)C.[CH:22]1[C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:32])[C:26]=2[CH:25]=[CH:24][N:23]=1.[CH2:33]([OH:35])[CH3:34]>>[C:33]([C:13]1[C:12]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:11][N:10]([CH2:8][CH3:9])[C:15](=[O:16])[C:14]=1[NH:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[CH:25]=[CH:24][N:23]=[CH:22]2)(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 702EthanolHCID 707665-AminoisoquinolineHCID 68893788HCID 68893788, compound

Product 1

HCID 67109556HCID 67109556, compoundYield 12.4%

Procedure

To a stirred solution of 80 mg (0.278 mmol) of 5-acetyl-2-ethyl-4-nitro-phenylpyridazin-3(2H)-one (Dal Piaz, V et al, J. Med. Chem. 1997, 40, 1417) in 4 ml of ethanol, 60 mg (0.417 mmol) of 5-isoquinolinamine was added. The resulting mixture was stirred at room temperature for three days. The final product was collected by filtration and purified by column chromatography (silica gel, ethyl acetate/hexane 7:3) to yield the title compound (20 mg, 12.4% yield).

Workup

  1. filtrationThe final product was collected by filtration
  2. custompurified by column chromatography (silica gel, ethyl acetate/hexane 7:3)

Sources & evidence

ORD record
ord-f6d4a171b6054e3494f89f37faac1fd9
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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