Ethanol → N-(2-(2-amino-3-benzyl-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-2-sulfonamide hydrochloride

HRID 82886Notes

Reaction equation

HRID 82886 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]([CH3:29])[CH:26]=[CH:27][N:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10][CH:9]1[NH:30]C(=O)OCC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].C(O)C.[ClH:41].C(OCC)C>[Cl-].[Na+].O>[ClH:41].[NH2:30][CH:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[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]([CH3:29])[CH:26]=[CH:27][N:28]=3)(=[O:23])=[O:22])[CH:15]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 10953452Ether hydrochlorideHCID 66740359ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-2-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 66741367N-(2-(2-amino-3-benzyl-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-2-sulfonamide hydrochloride

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To ethyl 1-benzyl-6-(2-(1-methyl-1H-imidazole-2-sulfonamido)ethoxy)-2,3-dihydro-1H-inden-2-ylcarbamate (26.7 mg, 0.054 mmol; see example 196) was added 2N potassium hydroxide in ethanol (4 mL, 8.00 mmol) and stirred at 90° C. for 1 h. 50% brine was added and extracted twice with dichloromethane. The combined organic layers were washed with brine, dried, filtered and evaporated to obtain a clear oil. Added 2N hydrochloric acid/diethyl ether and stirred at room temperature for 2 h, filtered, washed with diethyl ether and dried to obtain N-(2-(2-amino-3-benzyl-2,3-dihydro-1H-inden-5-yloxy)ethyl)-1-methyl-1H-imidazole-2-sulfonamide hydrochloride as a white solid. m=20.2 mg (54%)

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto obtain a clear oil
  7. stirringstirred at room temperature for 2 h
  8. filtrationfiltered
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-e2a7320c85c746e39e27cd9942fe79f0
Source dataset
uspto-grants-2014_09
Patent number
US08846743B2

Reaction notes

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