Sodium Hydroxide → N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 82887Notes

Reaction equation

HRID 82887 reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][C:31](=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][CH2:19][NH:20][S:21]([C:24]3[N:25]=[CH:26][N:27]([CH3:29])[CH:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30][CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56837048ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 56642612N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-4-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate (23.8 mg, 0.048 mmol; see example 195) in tetrahydrofuran (1 ml) was added lithium aluminium hydride in tetrahydrofuran (0.143 ml, 0.143 mmol) and the reaction mixture was refluxed for 2 h. Cooled down to room temperature and a 2N sodium hydroxide was slowly added and extracted twice with dichloromethane, washed with sodium bicarbonate and brine, dried, filtered and evaporated to obtain the crude material as white solid, that was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 10% methanol in dichloromethane over 25 min to afford N-(2-(3-benzyl-2-(methylamino)-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide as a clear glass. m=6.4 mg (23%)

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. extractionextracted twice with dichloromethane
  3. washwashed with sodium bicarbonate and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto obtain the crude material as white solid, that
  8. customwas purified by flash silica gel chromatography on 4 g SiO2-cartridge
  9. customover 25 min

Sources & evidence

ORD record
ord-9c93dc998ed241dbba34b64fa4bde435
Source dataset
uspto-grants-2014_09
Patent number
US08846743B2

Reaction notes

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