tert-Butylsulfonamide → 3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-5'-carboxylic acid (1-ethyl-1H-indol-6-yl)-amide
Reaction equation
N1(C2C=CC=CN=2)CCC(C(O)=O)CC1.C(OC([CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33](=[O:46])[NH:34][C:35]3[CH:43]=[C:42]4[C:38]([CH:39]=[CH:40][N:41]4[CH2:44][CH3:45])=[CH:37][CH:36]=3)=[CH:29][N:28]=2)[CH2:23][CH2:22]1)=O)C.C(S(N)(=O)=O)(C)(C)C.IC1C=CC(NC(C2C=CC(N3CCCCC3)=NC=2)=O)=CC=1C>>[CH2:44]([N:41]1[C:42]2[C:38](=[CH:37][CH:36]=[C:35]([NH:34][C:33]([C:30]3[CH:31]=[CH:32][C:27]([N:24]4[CH2:25][CH2:26][CH2:21][CH2:22][CH2:23]4)=[N:28][CH:29]=3)=[O:46])[CH:43]=2)[CH:39]=[CH:40]1)[CH3:45]Participants
Reactant 4
Product 1
Procedure
4-Methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (1-ethyl-1H-indol-6-yl)-amide was synthesized by the ECU coupling of 5″-ethyl-1H-indol-6-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (prepared by the hydrolysis of 5′-(1-ethyl-1H-indol-6-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester with LiOH monohydrate as described in the synthesis of 5′44-iodo-3-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid above.) with t-butyl sulfonamide in a manner similar to the one described in the synthesis of 442-methyl-propane-2-sulfonylaminocarbonyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-carboxylic acid (4-iodo-3-methyl-phenyl)-amide. LCMS calcd for C26H33N5O4S (m/e) 511, obsd 512 (M+H).
Sources & evidence
- ORD record
- ord-c72a8b1aae464a8c8741587ab2f4dd48
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324385B2
Reaction notes
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