Imidazole → HCID 21942622, compound

HRID 431988Notes

Reaction equation

HRID 431988 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16](F)[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)[O:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1.CN(C)C=O>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([N:27]3[CH:31]=[CH:30][N:29]=[CH:28]3)[CH:15]=[C:14]([C:19]#[N:20])[CH:13]=2)[O:9][N:8]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 98167783-Fluoro-5-(3-(pyridin-2-yl)-1,2,4-oxadiazol-5-yl)benzonitrile

Product 1

HCID 21942622HCID 21942622, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a screw cap vial equipped with stir bar added 3-(2-Pyridyl)-5-(3-cyano-5-fluorophenyl)-1,2,4-oxadiazole (20 mg, 0.08 mmol), potassium carbonate (20.8 mg, 0.15 mmol), imidazole (7.7 mg, 0.11 mmol) and dimethylformamide (1 ml). Stirred the resulting mixture at 120° C. for 2 h. The reaction mixture was diluted with chloroform (30 ml) and washed with water (30 ml). The aqueous phase was re-extracted with chloroform (30 ml) and the combined organic phase was dried (sodium sulfate), filtered and concentrated in-vacuo. The crude residue was purified on silica gel using 2% methanol in dichloromethane to isolate the free base of the desired compound as a white solid. The free base was converted to it's hydrochloride salt (10.0 mg), white solid. 1H-NMR (DMSO), δ (ppm): 9.85 (s, 1H), 8.86 (m, 4H), 8.49 (s, 1H), 8.23 (d, 1H), 8.13 (t, 1H), 7.95 (s, 1H), 7.73 (dd, 1H).

Workup

  1. customIn a screw cap vial
  2. customequipped
  3. stirringStirred the resulting mixture at 120° C. for 2 h
  4. washwashed with water (30 ml)
  5. extractionThe aqueous phase was re-extracted with chloroform (30 ml)
  6. dry with materialthe combined organic phase was dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customThe crude residue was purified on silica gel using 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-154fd4c3d0fc471b95ef7ff3b3c40701
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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