Cesium carbonate → Methyl 3-{[1-{[4-(tert-butylcarbamoyl)-2-methoxyphenyl]sulphonyl}-3-(4-chlorophenyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

HRID 536551Notes

Reaction equation

HRID 536551 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[NH:20][C:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:30][CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][C:40]1[CH:41]=[C:42]([CH:47]=[CH:48][CH:49]=1)[C:43]([O:45][CH3:46])=[O:44]>CN(C)C=O.O>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([N:17]2[C:21](=[O:22])[N:20]([CH2:39][C:40]3[CH:41]=[C:42]([C:43]([O:45][CH3:46])=[O:44])[CH:47]=[CH:48][CH:49]=3)[C:19]([C:23]3[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=3)=[N:18]2)(=[O:16])=[O:15])=[C:10]([O:30][CH3:31])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 135927695N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

Product 1

HCID 46238689Methyl 3-{[1-{[4-(tert-butylcarbamoyl)-2-methoxyphenyl]sulphonyl}-3-(4-chlorophenyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]methyl}benzenecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

An amount of 50 mg (0.108 mmol) of N-tert-butyl-4-{[3-(4-chlorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide from Example 14 and 53 mg (0.161 mmol) of caesium carbonate was suspended in 1 ml of dimethylformamide and admixed with 32 mg (0.140 mmol) of methyl 3-bromomethylbenzoate. The mixture was stirred at 60° C. overnight. The suspension was diluted with water. It was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvent on a rotary evaporator. The crude product was purified by preparative HPLC [Method 5]. This gave 40 mg (60% of theory) of the target compound.

Workup

  1. extractionIt was extracted twice with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. customfreed from the solvent on a rotary evaporator
  4. customThe crude product was purified by preparative HPLC [Method 5]

Sources & evidence

ORD record
ord-fea0321c9836479b86a9c2f62eabe9f8
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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