HCID 21254068, compound → HCID 70226981, compound

HRID 1531568Notes

Reaction equation

HRID 1531568 reaction equation
[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17]N)=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH3:4].[CH3:19][C:20]1[CH:21]=[C:22]([C:27]2[NH:28][C:29]3[C:34]([C:35]=2CCNCCCCC2C=CC(NS(C)(=O)=O)=CC=2)=CC(C(N2CCOCC2)=O)=CC=3)[CH:23]=[C:24]([CH3:26])[CH:25]=1>COCCO>[CH2:1]([N:5]1[CH:9]=[CH:8][N:7]=[C:6]1[CH2:10][C:11]1[CH:16]=[C:15]2[C:14](=[CH:13][CH:12]=1)[NH:17][C:27]([C:22]1[CH:21]=[C:20]([CH3:19])[CH:25]=[C:24]([CH3:26])[CH:23]=1)=[C:35]2[CH2:34][CH2:29][NH2:28])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21254068HCID 21254068, compoundHCID 70225153HCID 70225153, compound

Product 1

HCID 70226981HCID 70226981, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 350 mg (1.43 mmol) of (4-(1-butyl-1H-imidazol-2-ylmethyl)phenyl]hydrazine and 362 mg (1.72 mmol) of 3-chloropropyl 3,5-dimethylphenyl ketone (EXAMPLE 4) in 3 mL of 2-methoxyethanol was stirred at reflux under nitrogen for 3 hours. The solution was then cooled and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (elution with 95:5 CH2Cl2-MeOH followed by 95:5:0.5 CH2Cl2-MeOH-concd. NH4OH) gave 50 mg (9%) of material that was satisfactory for use in the next step.

Workup

  1. temperatureat reflux under nitrogen for 3 hours
  2. temperatureThe solution was then cooled
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (elution with 95:5 CH2Cl2-MeOH followed by 95:5:0.5 CH2Cl2-MeOH-concd. NH4OH)

Sources & evidence

ORD record
ord-2a0a43f9060343aa8b385ed51264bdb6
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

Loading…