5-bromoquinolin-8-amine → HCID 68483295, compound

HRID 1725532Notes

Reaction equation

HRID 1725532 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[CH:24]=[CH:25][C:26]([Br:33])=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2>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[CH:24]=[CH:25][C:26]([Br:33])=[C:27]2[C:32]=1[N:31]=[CH:30][CH:29]=[CH:28]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6138295-bromoquinolin-8-amineHCID 107320155-acetyl-2-ethylnitro6-phenylpyridazin-3(2H)-one

Product 1

HCID 68483295HCID 68483295, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 40 mg (0.139 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), 8-amino-5-bromoquinoline (47 mg, 0.209 mmol) was added. The resulting mixture was stirred at room temperature for five days and heated at 50° C. during four days. The solvent was evaporated and the residue purified by column chromatography (silica gel, hexane/ethyl acetate 4:1) to yield the title compound (16 mg, 25% yield).

Workup

  1. temperatureheated at 50° C. during four days
  2. customThe solvent was evaporated
  3. customthe residue purified by column chromatography (silica gel, hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-a413bf592a984bfb8705fd5f8347a280
Source dataset
uspto-grants-2009_02
Patent number
US07491722B2

Reaction notes

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