Phenyl chloroformate → HCID 58442676, compound

HRID 331116Notes

Reaction equation

HRID 331116 reaction equation
[O:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[C:3]([NH2:10])=[N:2]1.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13]>CC#N.O.C([O-])(O)=O.[Na+]>[C:15]1([O:14][C:12](=[O:13])[NH:10][C:3]2[C:4]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[O:1][N:2]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 15891Phenyl chloroformateHCID 13924712[1,2]Oxazolo[5,4-c]pyridin-3-amine

Product 1

HCID 58442676HCID 58442676, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of isoxazolo[5,4-c]pyridin-3-ylamine (1.49 g, 11.0 mmol) in CH3CN (50 mL) was added phenyl chloroformate (0.696 mL, 5.50 mmol). The reaction mixture was heated at 70° C. overnight, then cooled to rt, diluted with H2O (100 mL) and saturated aqueous NaHCO3 (10 mL). The resulting yellow precipitate was filtered and dried under vacuum to give isoxazolo[5,4-c]pyridin-3-yl-carbamic acid phenyl ester (1.099 g, 39%). MS (ESI+): calcd for C13H9N3O3 m/z 255.06, found 256.1 (M+H)+.

Workup

  1. temperaturecooled to rt
  2. filtrationThe resulting yellow precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-dc1c054d05d6479e8ff28a54620c796a
Source dataset
uspto-grants-2014_11
Patent number
US08877769B2

Reaction notes

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