4-(3-Fluoropropyl)-benzenesulfonyl chloride → 4-(3-Fluoro-propyl)-N-[2-methoxy-6-(2-pyrrolidin-1-yl-ethoxy)-pyridin-3-yl]-benzenesulfonamide
Reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][CH:6]=[C:5]([O:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[N:4]=1.[F:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>N1C=CC=CC=1>[F:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:9][C:8]2[C:3]([O:2][CH3:1])=[N:4][C:5]([O:10][CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:6][CH:7]=2)(=[O:30])=[O:29])=[CH:24][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
After a solution of 2-Methoxy-6-(2-pyrrolidin-1-yl-ethoxy)-pyridin-3-ylamine (200 mg, 0.84 mmol) in pyridine (3 ml) was stirred at room temperature for 30 minutes 4-(3-fluoro-propyl)-benzenesulfonyl chloride (200 mg, 0.84 mmol) was added. The mixture was stirred at room temperature for 16 h, thereafter the solvent was evaporated under reduced pressure. The residue was taken up in toluene and the solvent was evaporated. This procedure was repeated once. The residue was purified by silica gel chromatography with dichloromethane/methanol (100:0; 95:5; 0:100) as eluent to give 20 mg (5.4%) of the title compound.
Workup
- additionwas added
- customthe solvent was evaporated under reduced pressure
- customthe solvent was evaporated
- customThe residue was purified by silica gel chromatography with dichloromethane/methanol (100:0; 95:5; 0:100) as eluent
Sources & evidence
- ORD record
- ord-4274f0b5e05642d3b7eb5a874fccab67
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383641B2
Reaction notes
Loading…