1-Propanesulfonyl chloride → N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide
Reaction equation
[CH2:1]([S:4](Cl)(=[O:6])=[O:5])[CH2:2][CH3:3].[C:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21](=[O:37])[C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([NH:29][S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[C:23]=3[F:36])[CH:18]=2)[NH:13][CH:12]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[C:17]([NH:20][C:21](=[O:37])[C:22]3[C:27]([F:28])=[CH:26][CH:25]=[C:24]([N:29]([S:30]([CH2:33][CH2:34][CH3:35])(=[O:32])=[O:31])[S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[C:23]=3[F:36])[CH:18]=2)[N:13]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH:12]=1)(=[O:10])[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
TEA (0.0163 mL, 0.117 mmol) and propane-1-sulfonyl chloride (0.00882 mL, 0.0779 mmol) were added to N-(3-acetyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.195 mL, 0.0390 mmol) in DCM (0.4 mL). The solution was stirred at room temperature for 16 hours before concentration under reduced pressure. The resulting residue was purified via column chromatography (2% MeOH/DCM) to afford impure N-(3-acetyl-1-(propylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-2,6-difluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzamide (0.020 g, 0.0308 mmol, 79.1% yield).
Workup
- customThe resulting residue was purified via column chromatography (2% MeOH/DCM)
Sources & evidence
- ORD record
- ord-bc74b8d3ff6c4d5b96853969155882e6
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338452B2
Reaction notes
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