Iodoethane → HCID 17981769, compound

HRID 2252076Notes

Reaction equation

HRID 2252076 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:33])(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH2:34](N(CC)CC)[CH3:35].ICC>CN(C)C=O>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16]3[N:17]=[C:18]([CH:27]4[CH2:32][CH2:31][N:30]([CH2:34][CH3:35])[CH2:29][CH2:28]4)[NH:19][C:20]=3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:33])(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 11225063HCID 11225063, compound

Product 1

HCID 17981769HCID 17981769, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir a mixture of 1-isopropylsulfonyl-2-amino-6-(2-(piperidin-4-yl)-5-(phenyl)-imidazol-4-yl)-benzimidazole (0.574 g, 1.23 mmol), triethylamine (3.1 mmol), and iodoethane (1.54 mmol) in anhydrous dimethylformamide (5 mL) at room temperature for 6 hours. Partition the mixture between ethyl acetate and water. Extract the aqueous layer with ethyl acetate (3 times). Wash the combined organic layers sequentially with cold water (5 times) and saturated aqueous sodium chloride, dry over sodium sulfate, and concentrate under reduced pressure. Subject the residue to silica gel chromatography to provide the title compound in 76% yield. MS(ES+): m/z=493.2 (M+H)+

Workup

  1. customPartition the mixture between ethyl acetate and water
  2. extractionExtract the aqueous layer with ethyl acetate (3 times)
  3. washWash the combined organic layers sequentially with cold water (5 times) and saturated aqueous sodium chloride
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7e340d96a0664ae3b126a87d9e0c837a
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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