tert-Butylsulfonamide → N-(1-Ethyl-1H-indol-6-yl)-4-[4-(2-methyl-propane-2-sulfonylaminocarbonyl)-piperidin-1-yl]-benzamide
Reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][CH:24]([C:27](O)=[O:28])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)=[O:14])[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2].[C:30]([S:34]([NH2:37])(=[O:36])=[O:35])([CH3:33])([CH3:32])[CH3:31].IC1C=CC(NC(C2C=CC(N3CCC(C(NS(C(C)(C)C)(=O)=O)=O)CC3)=NC=2)=O)=CC=1C>>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:14])[C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][CH:24]([C:27]([NH:37][S:34]([C:30]([CH3:33])([CH3:32])[CH3:31])(=[O:36])=[O:35])=[O:28])[CH2:23][CH2:22]4)=[CH:17][CH:16]=3)[CH:10]=2)[CH:5]=[CH:4]1)[CH3:2]Participants
4
Reactant 3
Product 1
Procedure
N-(1-Ethyl-1H-indol-6-yl)-4-[4-(2-methyl-propane-2-sulfonylaminocarbonyl)-piperidin-1-yl]-benzamide was prepared form 1-[4-(1-ethyl-1H-indol-6-ylcarbamoyl)-phenyl]-piperidine-4-carboxylic acid and t-butyl sulfonamide in a manner similar to the one described in the synthesis of 4-(2-methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (4-iodo-3-methyl-phenyl)-amide. The product was isolated after a silica gel column purification with 50-100% Et2O in hexanes to 50-100% EtOAc in hexane gradient. HRMS m/z calcd for C27H34N4O4S [M+H]+: 511.2374. Found: 511.2372.
Workup
- customThe product was isolated
- customafter a silica gel column purification with 50-100% Et2O in hexanes to 50-100% EtOAc in hexane gradient
Sources & evidence
- ORD record
- ord-1274814f95b44e469b7cc7ab6ba17b2c
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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