3-Pentanol → HCID 58938535, compound

HRID 598139Notes

Reaction equation

HRID 598139 reaction equation
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:11]2[CH:21]=[CH:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=3[CH3:29])[C:12]=2[C:13](=[O:18])[N:14]([CH2:16][CH3:17])[N:15]=1>CN(C=O)C.O>[CH3:29][C:23]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=1[N:19]1[C:12]2[C:13](=[O:18])[N:14]([CH2:16][CH3:17])[N:15]=[C:10]([O:6][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[C:11]=2[CH:21]=[CH:20]1

Participants

6

Reactant 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 67267320HCID 67267320, compound

Product 1

HCID 58938535HCID 58938535, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-pentanol (0.079 ml, 0.73 mmol) in DMF (1 ml) was added sodium hydride (60% in oil, 29 mg, 0.73 mmol). The mixture was stirred for 10 min before addition of 4-chloro-1-(2,4-dimethylphenyl)-6-ethyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (55 mg, 0.18 mmol). The mixture was stirred at 60° C. for 4 hours, then diluted with water (30 ml) and extracted with ethyl acetate (50 ml). The extract were combined, washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with hexane/ethyl acetate (10:1) to give 48 mg (48%) of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate (50 ml)
  2. washwashed 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 (10:1)

Sources & evidence

ORD record
ord-0e8a255f173b422fb8c3d65fd58471c4
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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