Potassium Iodide → HCID 23132881, compound

HRID 2062092Notes

Reaction equation

HRID 2062092 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([NH:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[O:13].Cl[CH2:22][C:23]1[NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O>[NH:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[CH2:22][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([NH:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17])=[O:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 785712-ChloromethylbenzimidazoleHCID 23132830HCID 23132830, compound

Product 1

HCID 23132881HCID 23132881, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.45 g of the Wang-resin-bound 2-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid (loading 0.35 mmol/g) was placed in a reaction vessel with 3 ml of dimethylformamide. To this was added 0.058 g of 2-chloromethyl-1H-benzoimidazole, 0.228 g of cesium carbonate and 0.023 g of potassium iodide. The reaction was then placed in a vortex shaker overnight. The resin was filtered, washed four times each with dimethylformamide, methanol and dichloromethane. To this was added a solution of 30% trifluoroacetic acid, 65% dichloromethane and 5% triethylsilane and left in vortex shaker for 1.5 hours. The resin was filtered and the filtrate concentrated in vacuo. Purification by flash chromatography on silica with dichloromethane/methanol afforded 25 mg of 2-{[1-(1H-Benzoimidazol-2-ylmethoxy) naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid.

Workup

  1. customwas then placed in a vortex shaker overnight
  2. filtrationThe resin was filtered
  3. washwashed four times each with dimethylformamide, methanol and dichloromethane
  4. additionTo this was added a solution of 30% trifluoroacetic acid, 65% dichloromethane and 5% triethylsilane
  5. filtrationThe resin was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customPurification by flash chromatography on silica with dichloromethane/methanol

Sources & evidence

ORD record
ord-e9f3add9efca43c78c7e661bcab8992a
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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