Methanamine, N-methoxy-, hydrochloride (1:1) → 3-(4-Chloro-3-trifluoromethyl-benzenesulfonylamino)-5-methyl-pyridine-2-carboxylic acid methoxy-methyl-amide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([OH:21])=O)=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].Cl.[CH3:27][O:28][NH:29][CH3:30]>C1COCC1>[CH3:27][O:28][N:29]([CH3:30])[C:19]([C:13]1[C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=2)(=[O:10])=[O:9])=[CH:17][C:16]([CH3:18])=[CH:15][N:14]=1)=[O:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
10.49 g (26.6 mmol) of 3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-5-methyl-pyridine-2-carboxylic acid was reacted with 5.40 g (33.2 mmol) of N,N′-carbonyldiimidazole in 40 mL of refluxing THF for 3 h. The temperature was lowered to 50° C., 2.86 g (29.3 mmol) of O,N-dimethyl-hydroxylamine hydrochloride was added and the reaction was stirred overnight at 50° C. Half of the solvent was removed under reduced pressure and the reaction mixture was diluted with 200 mL of cold water. The solids were filtered off, washed with 100 mL of water and dried to give 9.8 g (84%) of the product as a tan powder.
Workup
- customwas lowered to 50° C.
- customHalf of the solvent was removed under reduced pressure
- additionthe reaction mixture was diluted with 200 mL of cold water
- filtrationThe solids were filtered off
- washwashed with 100 mL of water
- customdried
Sources & evidence
- ORD record
- ord-5a4fd9d2e275459fad0664cb9fa43794
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546408B2
Reaction notes
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