Sodium Hydroxide → HCID 18349599, compound

HRID 378633Notes

Reaction equation

HRID 378633 reaction equation
[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[CH2:25]([N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH2:37][CH2:38][CH:39]=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C.C(#N)C>[CH2:25]([N:32]1[CH:36]=[CH:35][N:34]=[C:33]1[CH2:37][CH2:38][CH2:39][NH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)(=[O:16])=[O:15])=[CH:7][CH:6]=1)([CH3:3])[CH3:4])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 18349572HCID 18349572, compoundHCID 18349790HCID 18349790, compound

Product 1

HCID 18349599HCID 18349599, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of N-{2-[4-(1-amino-1-methylethyl)phenyl]ethyl}-4-methoxybenzenesulphonamide (0.97 g), 3-(1-benzylimidazol-2-yl)propionaldehyde (0.66 g), 4A molecular sieves (0.7 g) and acetonitrile (15 ml) was stirred at ambient temperature for 18 hours. The mixture was filtered and the filtrate evaporated under reduced pressure to give a residue which was dissolved in absolute ethanol (15 ml). Sodium borohydride (0.18 g) was added to the ethanolic solution and the mixture was boiled under reflux for 3 hours. The solvent was removed under reduced pressure and water was added to the residue followed by dilute hydrochloric acid to give an acidic mixture. After 20 minutes the mixture was basified with dilute sodium hydroxide solution and extracted with ethyl acetate to give an oil which was purified with flash column chromatography on silica to give N-[2-(4-{1-[3-(1-benzylimidazol-2-yl)propylamino]-1-methylethyl}phenyl)ethyl]-4-methoxybenzenesulphonamide. A mixture of this product (0.61 g), absolute ethanol (30 ml), ammonium formate (0.42 g) and 10% palladium on carbon (0.91 g) was boiled under reflux for 1 hour. The mixture was filtered and the filtrate was evaporated under reduced pressure to give a residue which was purified by flash column chromatography on silica using ethyl acetate/methanol/triethylamine (18:1:1) as the mobile phase to give N-[2-(4-{1-[3-(imidazol-2-yl)propylamino]-1-methylethyl}phenyl)ethyl]-4-methoxybenzenesulphonamide as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customto give a residue which
  4. temperatureunder reflux for 3 hours
  5. customThe solvent was removed under reduced pressure and water
  6. additionwas added to the residue
  7. customto give an acidic mixture
  8. extractionextracted with ethyl acetate
  9. customto give an oil which
  10. customwas purified with flash column chromatography on silica

Sources & evidence

ORD record
ord-068dd66c2eee48bd99fba4ea1a550390
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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