Ethyl Acetate → HCID 178519373, compound

HRID 2110021Notes

Reaction equation

HRID 2110021 reaction equation
OI1(=O)C2C=CC=CC=2C(=O)O1.[C:13]1([CH2:23][N:24]2[CH2:29][CH2:28][CH:27]([CH2:30][NH:31][C:32]3[NH:36][C:35]4[CH:37]=[CH:38][C:39]([CH2:41][OH:42])=[CH:40][C:34]=4[N:33]=3)[CH2:26][CH2:25]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(OCC)(=O)C>CS(C)=O>[C:13]1([CH2:23][N:24]2[CH2:25][CH2:26][CH:27]([CH2:30][NH:31][C:32]3[NH:36][C:35]4[CH:37]=[CH:38][C:39]([CH:41]=[O:42])=[CH:40][C:34]=4[N:33]=3)[CH2:28][CH2:29]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 3394961-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxideHCID 178519374HCID 178519374, compound

Product 1

HCID 178519373HCID 178519373, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 1-hydroxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one (846 mg, 3.02 mmol) in dimethylsulfoxide (10 ml) was added to a solution of {2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazol-5-yl}-methanol (807 mg, 2.01 mmol) in dimethylsulfoxide (10 ml), and the mixture was stirred at room temperature for 9 hours. The reaction mixture was poured into ice water (200 ml) and stirred at room temperature for 30 minutes, after which ethyl acetate was added and stirring was continued vigorously for 10 minutes for extraction. After washing with saturated aqueous sodium bicarbonate and saturated brine, the mixture was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1). This was further purified by preparative HPLC to obtain 2-[(1-naphthalen-1-ylmethyl-piperidin-4-ylmethyl)-amino]-1H-benzimidazole-5-carboaldehyde.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. stirringstirring
  3. extractionwas continued vigorously for 10 minutes for extraction
  4. washAfter washing with saturated aqueous sodium bicarbonate and saturated brine
  5. dry with materialthe mixture was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol=9/1)
  8. customThis was further purified by preparative HPLC

Sources & evidence

ORD record
ord-96bdd5f1561c44baa3acb812f60e6128
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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