3-Bromopentane → HCID 67268316, compound

HRID 598150Notes

Reaction equation

HRID 598150 reaction equation
[NH2:1][C:2]1[C:3]2[CH:12]=[CH:11][N:10]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[C:5](=[O:9])[N:6](C)[N:7]=1.[H-].[Na+].Br[CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27]>CN(C=O)C.O>[C:14]1([CH3:21])[CH:15]=[C:16]([CH3:20])[CH:17]=[C:18]([CH3:19])[C:13]=1[N:10]1[C:4]2[C:5](=[O:9])[NH:6][N:7]=[C:2]([NH:1][CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:3]=2[CH:12]=[CH:11]1

Participants

6

Reactant 3

HCID 157383-BromopentaneHCID 24758Sodium hydrideHCID 67266934HCID 67266934, compound

Product 1

HCID 67268316HCID 67268316, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-amino-1-mesityl-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-one (113 mg, 0.40 mmol) in DMF (1 ml) were added sodium hydride (60% in oil, 48 mg, 1.20 mmol) and 3-bromopentane (0.15 ml, 1.20 mmol). The mixture was stirred at 80° C. for 15 hours, then diluted 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 column chromatography eluting with hexane/ethyl acetate (5:1) to give 35 mg (25%) of the title compound as crystals.

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 column chromatography
  6. washeluting with hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-b971ea18a1f14f6e89c29d825115ef14
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…