Ethyl Acetate → HCID 131724969, compound

HRID 1070410Notes

Reaction equation

HRID 1070410 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([CH2:15][O:16][C:17](=[O:33])[NH:18]C4C=CC(C5C=CC=CC=5)=CC=4C#N)=[CH:12][C:11]=3[CH:34]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CN(C=O)C>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([CH2:15][O:16][C:17](=[O:33])[NH2:18])=[CH:12][C:11]=3[CH:34]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22396310HCID 22396310, compound

Product 1

HCID 131724969HCID 131724969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of (3-cyano-biphenyl-4-yl)-carbamic acid-5-phenyl-benzofuran-2-yl-methylester (0.40 g, 0.90 mmol), sodium azide (0.117 g, 1.80 mmol) and ammonium chloride (0.096 g, 1.80 mmol) in 3 mL DMF was heated to 90° C. under a nitrogen atmosphere for 20 h. The mixture was cooled to room temperature, ethyl acetate was added and the solution was washed with 1M HCl, followed by water, dried and concentrated to dryness. Purification by chromatography gave 72 mg of 3-(1H-tetrazol-5-yl)-biphenyl-4-yl]-carbamic acid 5-phenyl-benzofuran-2-ylmethyl ester 501, mp: 180-183° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washthe solution was washed with 1M HCl
  3. customdried
  4. concentrationconcentrated to dryness
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-11ea0879084a4b61b1a83657993d1933
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

Loading…