Cesium carbonate → N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

HRID 536552Notes

Reaction equation

HRID 536552 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][CH:40]([OH:45])[C:41]([F:44])([F:43])[F:42]>CN(C)C=O.[Cl-].[NH4+]>[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][CH:40]([OH:45])[C:41]([F:44])([F:43])[F:42])[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 2206323-Bromo-1,1,1-Trifluoro-2-PropanolHCID 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 46238690N-tert-Butyl-4-{[3-(4-chlorophenyl)-5-oxo-4-(3,3,3-trifluoro-2-hydroxypropyl)-4,5-dihydro-1H-1,2,4-triazol-1-yl]sulphonyl}-3-methoxybenzenecarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
75 °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 were suspended in 1 ml of dimethylformamide and admixed with 26 μl (0.161 mmol) of 3-bromo-1,1,1-trifluoro-2-propanol. The mixture was stirred at 75° C. for 8 hours. The suspension was diluted with saturated aqueous ammonium chloride solution. 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 22 mg (36% 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-ae72c616a87d430a901e16bb54021a72
Source dataset
uspto-grants-2014_10
Patent number
US08859601B2

Reaction notes

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