Cesium carbonate → 5-(4-Chlorophenyl)-4-(4-methoxybenzyl)-2-(1H-1,2,4-triazol-5-ylsulfonyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:29]1[C:33]([S:34](Cl)(=[O:36])=[O:35])=[N:32][CH:31]=[N:30]1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:10](=[O:13])[N:11]([S:34]([C:33]3[NH:29][N:30]=[CH:31][N:32]=3)(=[O:36])=[O:35])[N:12]=2)=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
529 mg (1.68 mmol) of 5-(4-chlorophenyl)-4-(4-methoxybenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one [preparation according to WO 2007/134862 Example 55A] were dissolved in 10 ml of acetonitrile, and 1.09 g (3.35 mmol) of cesium carbonate and 281 mg (1.68 mmol) of 1H-1,2,4-triazole-5-sulfonyl chloride, dissolved in 5 ml of acetonitrile, were added successively. The reaction mixture was stirred at RT for 90 min. For work-up, 10 g of silica gel were added and the solvent was removed under reduced pressure. The crude product, adsorbed on silica gel, was purified by chromatography on silica gel (mobile phase: first ethyl acetate, then dichloromethane/methanol 90:10→80:20). This gave 268 mg (32% of theory) of the target compound.
Workup
- additionwere added successively
- additionFor work-up, 10 g of silica gel were added
- customthe solvent was removed under reduced pressure
- customwas purified by chromatography on silica gel (mobile phase
Sources & evidence
- ORD record
- ord-7c94e93c00cb41a49da542deb2641d44
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187466B2
Reaction notes
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