Potassium Carbonate → N-methylsulfonyl-2-[4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenoxy]-propionamide

HRID 1090981Notes

Reaction equation

HRID 1090981 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:6][C:5]([N:16]2[C:20](=[O:21])[N:19]([CH:22]([F:24])[F:23])[C:18]([CH3:25])=[N:17]2)=[C:4]([F:26])[CH:3]=1.[CH3:27][S:28]([NH:31][C:32](=[O:36])[CH:33](Br)[CH3:34])(=[O:30])=[O:29].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:27][S:28]([NH:31][C:32](=[O:36])[CH:33]([O:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[CH:6]=[C:5]([N:16]3[C:20](=[O:21])[N:19]([CH:22]([F:23])[F:24])[C:18]([CH3:25])=[N:17]3)[C:4]([F:26])=[CH:3][C:2]=2[Cl:1])=[CH:10][CH:11]=1)[CH3:34])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14554242N-methylsulfonyl-2-bromopropionamideHCID 199122251-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one

Product 1

HCID 19912237N-methylsulfonyl-2-[4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenoxy]-propionamideYield 40.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to Step D of Example 1, the reaction of 0.60 g (0.0015 mole) of 1-[4-chloro-2-fluoro-5-(4-hydroxyphenoxy)phenyl]-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, 0.32 g (0.0014 mole) of N-methylsulfonyl-2-bromopropionamide, and 0.24 g (0.0017 mole) of potassium carbonate in 20 mL of acetone produced 0.3 g of N-methylsulfonyl-2-[4-[2-chloro-4-fluoro-5-(4-difluoromethyl-4,5 -dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)phenoxy]phenoxy]-propionamide as an oil, Compound 32 of Table 1.

Sources & evidence

ORD record
ord-1d2bbb9f04544b09b88a3484df5fbd67
Source dataset
uspto-grants-1992_01
Patent number
US05084085

Reaction notes

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