Triethylamine → N-({[2-(4-{2-Ethyl-5-[1-(methyloxy)ethyl]-1H-benzimidazol-1-YL]phenyl)ethyl]amino}carbonyl)-4-methylbenzenesulfonamide

HRID 2077804Notes

Reaction equation

HRID 2077804 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:10][CH:9]=2)[C:6]2[CH:30]=[CH:31][C:32]([CH:34]([OH:36])[CH3:35])=[CH:33][C:5]=2[N:4]=1)[CH3:2].S(Cl)(Cl)=O.[CH2:41](N(CC)CC)C>C(Cl)Cl>[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])=[O:18])=[CH:10][CH:9]=2)[C:6]2[CH:30]=[CH:31][C:32]([CH:34]([O:36][CH3:41])[CH3:35])=[CH:33][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 21876255N-[{(2-{4-[2-ethyl-5-(1-hydroxyethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide

Product 1

HCID 21875610N-({[2-(4-{2-Ethyl-5-[1-(methyloxy)ethyl]-1H-benzimidazol-1-YL]phenyl)ethyl]amino}carbonyl)-4-methylbenzenesulfonamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[{(2-{4-[2-ethyl-5-(1-hydroxyethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide (Example 345, 151 mg, 0.3 mmol) in CH2Cl2 (15 ml) was added thionyl chloride (0.1 ml, 1.5 mmol) at room temperature. The mixture was stirred at room temperature for 2 h. The solvent was removed and the residue was dissolved with methanol (15 ml). The mixture was added triethylamine (0.08 ml, 0.6 mmol) and stirred at room temperature for 5 h. The solvent was removed and the residue was extracted with CH2Cl2 (50 ml). The organic layer was washed with water (10 ml), brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (1:6)/CH2Cl2:methanol (10:1) to afford 139 mg (89%) of the title compound as white solids.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved with methanol (15 ml)
  3. stirringstirred at room temperature for 5 h
  4. customThe solvent was removed
  5. extractionthe residue was extracted with CH2Cl2 (50 ml)
  6. washThe organic layer was washed with water (10 ml), brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. customAfter removal of solvent
  9. customthe crude product was purified by flash column chromatography
  10. washeluting with hexane/ethyl acetate (1:6)/CH2Cl2:methanol (10:1)

Sources & evidence

ORD record
ord-9cf822ff6b2d4d689ed5a021ac95ee66
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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