Imidazole → HCID 21942608, compound

HRID 431987Notes

Reaction equation

HRID 431987 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[O:12][N:11]=2)[CH:6]=[C:7](F)[CH:8]=1)#[N:2].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>[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[O:12][N:11]=2)[CH:6]=[C:7]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21942491HCID 21942491, compound

Product 1

HCID 21942608HCID 21942608, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a screw cap vial equipped with stir bar added 3-(3-Cyano-5-fluorophenyl)-5-(2-Pyridyl)-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 1% 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 (11.7 mg), white solid. 1H-NMR (DMSO), δ (ppm): 9.81 (s, 1H), 8.83 (m, 4H), 8.42 (m, 2H), 8.19 (dt, 1H), 7.92 (s, 1H), 7.80 (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 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-9981cf7b926848ecaddfc957c322fc3b
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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