Sodium Hydroxide → N-[{(2-{4-[2-ethyl-5-(1-hydroxyethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamide

HRID 2077803Notes

Reaction equation

HRID 2077803 reaction equation
[C:1]([C:4]1[CH:36]=[CH:35][C:7]2[N:8]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:22]([NH:24][S:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)(=[O:27])=[O:26])=[O:23])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].[BH4-].[Na+].[NH4+].[Cl-]>C(O)C.O>[CH2:11]([C:9]1[N:8]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:22]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=3)(=[O:27])=[O:26])=[O:23])=[CH:15][CH:14]=2)[C:7]2[CH:35]=[CH:36][C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]=2[N:10]=1)[CH3:12]

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21875662HCID 21875662, compound

Product 1

HCID 21876255N-[{(2-{4-[2-ethyl-5-(1-hydroxyethyl)-1H-benzimidazol-1-yl]phenyl}ethyl)amino]carbonyl}-4-methylbenzenesulfonamideYield 83.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture N-[({2-[4-(5-acetyl-2-ethyl-1H-benzimidazol-1-yl)phenyl]ethyl}amino)carbonyl]-4-methylbenzenesulfonamide (Example 78, 238 mg, 0.47 mmol) and 2N NaOH (0.1 ml) in ethanol (10 ml) was added a mixture of NaBH4 (178 mg, 0.47 mmol) and 2N NaOH (0.1 ml) in ethanol (4 ml) at room temperature. The mixture was stirred at room temperature for 4 h. The mixture was added water (10 ml) and neutralized with NH4Cl. The mixture was extracted with ethyl acetate (50 ml). The organic layer was washed with brine (10 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (1:4/1:6)/CH2Cl2:methanol (10:1) to afford 198 mg (83%) of the title compound as white solids.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (50 ml)
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography
  6. washeluting with hexane/ethyl acetate (1:4/1:6)/CH2Cl2:methanol (10:1)

Sources & evidence

ORD record
ord-27cfae456d234e269d8a7d16d6299c6d
Source dataset
uspto-grants-2011_04
Patent number
US07928119B2

Reaction notes

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