tert-Butylsulfonamide → 4-(2-Methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (3-iodo-4-methyl-phenyl)-amide
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:27]([S:31]([NH2:34])(=[O:33])=[O:32])([CH3:30])([CH3:29])[CH3:28].IC1C=CC(NC(C2C(N3CCC(C(NS(C(C)(C)C)(=O)=O)=O)CC3)=CC=NC=2)=O)=CC=1C>>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([NH:34][S:31]([C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:33])=[O:32])=[O:25])[CH2:20][CH2:19]3)=[N:16][CH:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[CH3:8]Participants
4
Reactant 3
Product 1
Procedure
4-(2-Methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (3-iodo-4-methyl-phenyl)-amide was prepared from 5′-(3-Iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-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-[1,4]bipyridinyl-5′-carboxylic acid (4-iodo-3-methyl-phenyl)-amide. The product was isolated after a silica gel column purification with 2-5% MeOH in CH2Cl2. HRMS m/z calcd for C23H29N4O4SI [M+H]+: 585.1027. Found: 585.1027.
Workup
- customThe product was isolated
- customafter a silica gel column purification with 2-5% MeOH in CH2Cl2
Sources & evidence
- ORD record
- ord-affd20096748456595cc0a14881ab09a
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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