Water → HCID 11515618, compound

HRID 598135Notes

Reaction equation

HRID 598135 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:11]2[CH:20]=[CH:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH3:28])[C:12]=2[C:13](=[O:17])[N:14]([CH3:16])[N:15]=1.O>CN(C=O)C>[CH3:28][C:22]1[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:21]=1[N:18]1[C:12]2[C:13](=[O:17])[N:14]([CH3:16])[N:15]=[C:10]([O:6][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[C:11]=2[CH:20]=[CH:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 114283-PentanolHCID 24758Sodium hydrideHCID 67268082HCID 67268082, compound

Product 1

HCID 11515618HCID 11515618, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution 3-pentanol (0.064 ml, 0.60 mmol) in DMF (1 ml) was added sodium hydride (60% in oil, 24 mg, 0.60 mmol). The mixture was stirred for 10 min before addition of 4-chloro-1-(2,4-dimethylphenyl)-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (43.2 mg, 0.15 mmol). The mixture was stirred at 60° C. for 3 hours, then dilated with water (30 ml) and extracted with ethyl acetate (50 ml). The extract was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (5:1) to give 48 mg (94%) of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-6383d50137984652bb7b3db5db01549a
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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