Potassium Carbonate → N-(3-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-benzenesulphonamide

HRID 1010580Notes

Reaction equation

HRID 1010580 reaction equation
C(O[CH:4](O)[C:5]([C:7]1[CH:8]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:10]=[CH:11][CH:12]=1)=[O:6])C.[I:24][C:25]1[N:26]=[CH:27][N:28]([CH2:30][CH2:31][C:32]([NH2:35])([CH3:34])[CH3:33])[CH:29]=1.[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:6][CH:5]([C:7]1[CH:8]=[C:9]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH:10]=[CH:11][CH:12]=1)[CH2:4][NH:35][C:32]([CH3:34])([CH3:33])[CH2:31][CH2:30][N:28]1[CH:29]=[C:25]([I:24])[N:26]=[CH:27]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 210945453-(4-Iodo-imidazol-1-yl)-1,1-dimethyl-propylamineHCID 57429080N-[3-(2-ethoxy-2-hydroxyacetyl)-phenyl]-benzenesulphonamide

Product 1

HCID 11497696N-(3-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-benzenesulphonamideYield 45.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

7.81 g (23.3 mmol) N-[3-(2-ethoxy-2-hydroxy-acetyl)-phenyl]-benzenesulphonamide and 6.50 g (23.3 mmol) 3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamine in 40 mL ethanol were refluxed for 15 h. The reaction mixture was cooled to 0° C. and then combined with 3.70 g (97.9 mmol) sodium borohydride. It was stirred for a further 24 h at ambient temperature stirred and then combined with 20 mL saturated aqueous potassium carbonate solution. The aqueous phase was separated from the organic phase and extracted twice with 50 mL ethyl acetate. The combined organic phases were washed with 20 mL saturated, aqueous sodium chloride solution, dried over magnesium sulphate and freed from the solvent using the rotary evaporator. The residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]. 12.9 g (10.5 mmol, 45%) N-(3-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-benzenesulphonamide were obtained as a colourless solid.

Workup

  1. stirringstirred
  2. customThe aqueous phase was separated from the organic phase
  3. extractionextracted twice with 50 mL ethyl acetate
  4. washThe combined organic phases were washed with 20 mL saturated
  5. dry with materialaqueous sodium chloride solution, dried over magnesium sulphate
  6. customthe rotary evaporator
  7. customThe residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]

Sources & evidence

ORD record
ord-60878d875b6f4ecfb50e41d575cf7441
Source dataset
uspto-grants-2011_07
Patent number
US07977334B2

Reaction notes

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