HCID 59475093, compound → HCID 59475102, compound
Reaction equation
BrC1S[C:4](Cl)=[C:5]([Cl:23])[C:6]=1[CH2:7][CH:8]([NH:10][C:11]([C:13]1[C:14]([C:19]([F:22])([F:21])F)=[N:15][N:16]([CH3:18])[CH:17]=1)=[O:12])[CH3:9].[Br:25][C:26]1[S:30]C(Cl)=C(CC(NC(C2C(C(F)(F)F)=NN(C)C=2)=O)C)C=1Cl.ClC1SC(Cl)=C(Cl)C=1CC(NC(C1C(C(F)(F)F)=NN(C)C=1)=O)C>>[Br:25][C:26]1[S:30][C:6]([CH2:7][CH:8]([NH:10][C:11]([C:13]2[C:14]([CH:19]([F:21])[F:22])=[N:15][N:16]([CH3:18])[CH:17]=2)=[O:12])[CH3:9])=[C:5]([Cl:23])[CH:4]=1Participants
Procedure
In a sulfonation flask 2.07 g (7.2 mmol) of the amine isomer mixture prepared in example P5b) and 1.45 g (14.4 mmol) triethylamine are dissolved in 50 ml of methylenechloride. Then a mixture of 1.65 g (7.2 mmol) 3-trifluoromethyl-1-methyl-1-H-pyrazole 4-carboxylic acid chloride and 50 ml methylenechloride is added at room temperature under stirring. After stirring for 16 hours the solvent is evaporated in a water jet vacuum and the residue purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:2-2:1). 1.52 g of an isomeric mixture of amides is obtained in the form of slightly brown crystals (m.p.: 134-138° C.). The mixture consists of 27% of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(2-bromo-4,5-dichlorothiophen-3-yl)-1-methylethyl]amide, 30% of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(5-bromo-2,4-dichlorothiophen-3-yl)-1-methylethyl]amide and 43% of the undesired 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid [2-(2,4,5-trichlorothiophen-3-yl)-1-methylethyl]amide.
Sources & evidence
- ORD record
- ord-8bd044e2385d4fbab392a05cd0563edb
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486986B2
Reaction notes
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