Water → HCID 23442480, compound

HRID 2119655Notes

Reaction equation

HRID 2119655 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[C:8](=[O:16])[C:7]2[N:17]([CH3:20])[N:18]=[CH:19][C:6]1=2)[CH3:4].I[CH2:22][CH2:23]CC.O>O1CCCC1>[CH2:3]([N:5]1[C:14]2[CH:13]=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[C:8](=[O:16])[C:7]2[N:17]([CH3:20])[N:18]=[CH:19][C:6]1=2)[CH2:4][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 23442433HCID 23442433, compound

Product 1

HCID 23442480HCID 23442480, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (60-72% in mineral oil, 38 mg, 0.94 mmol) in tetrahydrofuran (2 ml) was added a suspension of 1,7-dimethyl-1,4-dihydro-9H-pyrazolo[4,3-b]quinolin-9-one (EXAMPLE 47, step 2, 100 mg, 0.469 mmol) in tetrahydrofuran (5 ml) at 0° C. After 30 min, 1-iodobutane (0.11 ml, 0.94 mmol) was added. The mixture was stirred at room temperature for 3 h and at 70° C. for 4 h. After cooling to room temperature, water (30 ml) was added and extracted with ethyl acetate (50 ml×2). The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The obtained solid was washed with hexane to give 67 mg (53%) of the title compound as a yellow solid.

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate (50 ml×2)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. washThe obtained solid was washed with hexane

Sources & evidence

ORD record
ord-9717451cfd0244f788fa9f66f4970747
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

Loading…