Diisopropylethylamine → HCID 66700199, compound

HRID 1910716Notes

Reaction equation

HRID 1910716 reaction equation
Cl.Cl.[NH2:3][CH:4]([CH3:15])[CH2:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1Cl)=[O:7].C(N(C(C)C)CC)(C)C>O>[O:7]=[C:6]1[C:8]2[C:13](=[CH:12][CH:11]=[N:10][CH:9]=2)[NH:3][CH:4]([CH3:15])[CH2:5]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 66700119HCID 66700119, compound

Product 1

HCID 66700199HCID 66700199, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[Step 3] 64 mg of the crude product of 3-amino-1-(4-chloropyridin-3-yl)butan-1-one dihydrochloride were dissolved in 2 mL of N-dimethylformamide followed by adding 0.18 mL of diisopropylethylamine while cooling with ice and stirring for 1 hour at room temperature. This was followed by additionally stirring overnight at 100° C. Following completion of the reaction, water was added followed by extracting three times with chloroform. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (methanol:chloroform=1:10) to obtain 9 mg of 4-oxo-2-methyl-2,3-dihydro-1H-[1,6]naphthyridine in the form of a pale yellow oil (27%).

Workup

  1. temperaturewhile cooling with ice
  2. stirringby additionally stirring overnight at 100° C
  3. additionwas added
  4. extractionby extracting three times with chloroform
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-c1f129f6db9f4176a24e6507a265ea33
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

Loading…