5-Methylthiophene-2-sulfonyl chloride → N-[1-{[3-Fluoro-4-(methyloxy)phenyl]methyl}-4-(methyloxy)-1H-indazol-3-yl]-5-methyl-2-thiophenesulfonamide
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=3)[C:13]([NH2:22])=[N:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH3:23][C:24]1[S:28][C:27]([S:29](Cl)(=[O:31])=[O:30])=[CH:26][CH:25]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH2:10][N:11]2[C:19]3[C:14](=[C:15]([O:20][CH3:21])[CH:16]=[CH:17][CH:18]=3)[C:13]([NH:22][S:29]([C:27]3[S:28][C:24]([CH3:23])=[CH:25][CH:26]=3)(=[O:31])=[O:30])=[N:12]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-{[3-fluoro-4-(methyloxy)phenyl]methyl}-4-(methyloxy)-1H-indazol-3-amine (for a preparation see Intermediate 80) (130 mg, 0.8 mmol) in pyridine (2 mL) was added to 5-methyl-2-thiophenesulfonyl chloride (0.24 mmol). The reaction mixture was shaken briefly and allowed to stand for 3 h at 21° C. prior to concentration by blowdown. The residue was dissolved in 1:1 MeOH-DMSO (1 mL) and purified by Mass Directed AutoPrep on Xbridge column using Acetonitrile Water with an ammonium carbonate modifier (Method C). The solvent was evaporated in vacuo to give the title compound (76 mg) LCMS (System A) RT=1.11 min, ES+ve m/z 462 (M+H)+.
Workup
- concentrationto concentration by blowdown
- dissolutionThe residue was dissolved in 1:1 MeOH-DMSO (1 mL)
- custompurified by Mass Directed AutoPrep on Xbridge column
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-57dbb5ff902e40b68804564afa258100
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507543B2
Reaction notes
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