Triethylamine → 3-Phenyl-3-(pyridazin-4-yl)propanoyl azide

HRID 512197Notes

Reaction equation

HRID 512197 reaction equation
[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)[CH2:8][C:9](O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.C1C=CC(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.O>[C:1]1([CH:7]([C:12]2[CH:17]=[CH:16][N:15]=[N:14][CH:13]=2)[CH2:8][C:9]([N:39]=[N+:40]=[N-:41])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 867162233-Phenyl-3-(pyridazin-4-yl)propanoic acid

Product 1

HCID 867162243-Phenyl-3-(pyridazin-4-yl)propanoyl azide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-phenyl-3-(pyridazin-4-yl)propanoic acid (570 mg, 2.5 mmol) in DMF (30 mL) was added Et3N (505 mg, 5.0 mmol), followed by the DPPA (722 mg, 2.6 mmol) in portions at 0° C., the resulting mixture was stirred at room temperature for 1.5 hour. The reaction was diluted with water, extracted with AcOEt (3×40 ml), the combined organic layer was washed by brine, dried over Na2SO4 and concentrated to get the 3-phenyl-3-(pyridazin-4-yl)propanoyl azide (crude 650 mg), which was used for next step directly.

Workup

  1. extractionextracted with AcOEt (3×40 ml)
  2. washthe combined organic layer was washed by brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f2583ab1ea2240319afd636ea3396071
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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