Imidazole → HCID 178501117, compound

HRID 1053823Notes

Reaction equation

HRID 1053823 reaction equation
[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=O)[NH2:2].N1C=CN=C1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)#[N:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24813Phosphorus oxychlorideHCID 178501131HCID 178501131, compound

Product 1

HCID 178501117HCID 178501117, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the compound prepared in Example 21 (0.84 g, 4.6 mmol) in pyridine (20 mL) was added imidazole (1.0 g, 4.6 mmol) and phosphorusoxychloride (1.0 mL) in one portion at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 h whereupon the reaction was quenched with water and extracted with ethyl acetate. The organic extract was washed with 2 M hydrochloric acid, dried and concentrated to give the title compound (0.76 g, 99%) as a white solid.

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with 2 M hydrochloric acid
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8e645864c4a845ca8e579c0464bed558
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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