Ethanol → 2-(2,2-Dimethylpropyl)-5-(isopropylsulfonyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazole

HRID 1817856Notes

Reaction equation

HRID 1817856 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([CH:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:14][CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[C:22]([CH2:26][C:27](Cl)=O)([CH3:25])([CH3:24])[CH3:23].[OH-].[Na+].C(O)C>C(OCC)(=O)C>[CH3:23][C:22]([CH3:25])([CH3:24])[CH2:26][C:27]1[N:14]([CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH:11]([CH3:12])[CH3:13])(=[O:9])=[O:10])=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 815143,3-Dimethylbutanoyl chlorideHCID 688708672-Amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzene

Product 1

HCID 115456142-(2,2-Dimethylpropyl)-5-(isopropylsulfonyl)-1-(2-pyrrolidin-1-ylethyl)-1H-benzimidazoleYield 70.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-4-(isopropylsulfonyl)-1-(N-2-pyrrolidine-1-ylethylamino)benzene (122.9 mg, 0.39 mmol) in ethyl acetate (8 mL) was added tert-butylacetyl chloride (60 μL, 0.43 mmol) at room temperature, and the mixture was stirred for 1 h at room temperature. 2N—NaOH (1 mL) and ethanol (3 mL) were then added to the reaction mixture at room temperature, and stirred for 6 h at 80° C. The reaction was quenched with water, and extracted with three times with ethyl acetate. The combined organic layers were dried over MgSO4 and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=3:1) to give the title compound as an orange solid (107.9 mg, 70%).

Workup

  1. stirringstirred for 6 h at 80° C
  2. customThe reaction was quenched with water
  3. extractionextracted with three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customThe residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0fcac1db94bd4ad88dc45d8f47fb7cd6
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

Loading…