Cesium carbonate → 4-Allyl-5-(4-chlorophenyl)-2-{[1-(2,6-dichlorobenzyl)-1H-imidazol-5-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714719Notes

Reaction equation

HRID 714719 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][CH:15]=[CH2:16])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.Cl[CH2:18][C:19]1[N:23]([CH2:24][C:25]2[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:32])[CH:22]=[N:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CO>[CH2:14]([N:9]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[N:12][N:11]([CH2:18][C:19]2[N:23]([CH2:24][C:25]3[C:26]([Cl:32])=[CH:27][CH:28]=[CH:29][C:30]=3[Cl:31])[CH:22]=[N:21][CH:20]=2)[C:10]1=[O:13])[CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 497656025-(4-chlorophenyl)-4-allyl-2,4-dihydro-3H-1,2,4-triazol-3-oneHCID 674100415-(Chloromethyl)-1-(2,6-dichlorobenzyl)-1H-imidazole

Product 1

HCID 533787294-Allyl-5-(4-chlorophenyl)-2-{[1-(2,6-dichlorobenzyl)-1H-imidazol-5-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

41 mg (0.17 mmol) of the compound from Example 12A were dissolved in 2 ml of DMF, and 48 mg (0.17 mmol) of the compound from Example 40A and 85 mg (0.26 mmol) of cesium carbonate were added. The mixture was stirred at 80° C. for 16 h. After cooling to RT, the reaction mixture was diluted with 1 ml of methanol and directly purified chromatographically [Method 19]. This gave 4 mg (5% of theory) of the target compound.

Workup

  1. temperatureAfter cooling to RT
  2. customdirectly purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-06b4beec6938460d9e5d459f06778276
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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