(2-Bromoethoxy)-tert-butyldimethylsilane → 5-Chloro-thiophene-2-carboxylic acid {2-[[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide
Reaction equation
Br[CH2:2][CH2:3][O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[CH:12]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][S:22]([CH2:25][CH2:26][NH:27][C:28]([C:30]2[S:31][C:32]([Cl:35])=[CH:33][CH:34]=2)=[O:29])(=[O:24])=[O:23])[CH2:17][CH2:16]1)([CH3:14])[CH3:13]>>[C:8]([Si:5]([CH3:7])([CH3:6])[O:4][CH2:3][CH2:2][N:21]([CH:18]1[CH2:19][CH2:20][N:15]([CH:12]([CH3:14])[CH3:13])[CH2:16][CH2:17]1)[S:22]([CH2:25][CH2:26][NH:27][C:28]([C:30]1[S:31][C:32]([Cl:35])=[CH:33][CH:34]=1)=[O:29])(=[O:23])=[O:24])([CH3:11])([CH3:10])[CH3:9]Participants
3
Reactant 2
Product 1
Procedure
5-Chloro-thiophene-2-carboxylic acid {2-[[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 2.3 ml (3.5 equiv.) (2-bromo-ethoxy)-tert-butyl-dimethyl-silane and 1.2 g (3.05 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide. 5-Chloro-thiophene-2-carboxylic acid {2-[[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was obtained as crude material which was pure enough for further transformations.
Workup
- custom5-Chloro-thiophene-2-carboxylic acid {2-[[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-(1-isopropyl-piperidin-4-yl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure
Sources & evidence
- ORD record
- ord-df8bbd7be9c74a3ba7bc0a902b0e9e2c
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088925B2
Reaction notes
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