Water → HCID 18919219, compound

HRID 1291266Notes

Reaction equation

HRID 1291266 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][N:13]3[C:17]4[C:18](Cl)=[N:19][N:20]([CH3:23])[C:21](=[O:22])[C:16]=4[N:15]=[CH:14]3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:29][O-:30].[Na+].CO.O>CO>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH2:12][N:13]3[C:17]4[C:18]([O:30][CH3:29])=[N:19][N:20]([CH3:23])[C:21](=[O:22])[C:16]=4[N:15]=[CH:14]3)=[CH:25][CH:26]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18918893HCID 18918893, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 18919219HCID 18919219, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The procedure of Example 34 was repeated except that 1-[4-(4-chlorobenzoyl)benzyl]-5-methyl-7-chloroimidazo[4,5-d]pyridazin-4(5H)-one was used as the starting compound. Thus, this starting compound (52 mg) was dissolved in methanol (5 ml) followed by addition of 28% sodium methoxide/methanol (0.5 ml), and the mixture was refluxed for 3 hours. To this reaction mixture was added a large quantity of water and the resulting crystals were rinsed with water and dried under reduced pressure to provide 20 mg (yield 39%) of the title compound. 1H-NMR (CD3OD) δ: 3.73(3H,s), 3.97(3H,s), 5.70(2H,s), 7.41(2H,d,J=8.4Hz), 7.51(2H,d,J=8.8Hz), 7.73(2H,d,J=8.6Hz), 7.76(2H,d,J=8.2Hz), 8.36(1H,s).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. washthe resulting crystals were rinsed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-3a35b91a5d144730b78272355471fb05
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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