Water → HCID 178457108, compound

HRID 450725Notes

Reaction equation

HRID 450725 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:19][C:20]2[CH:34]=[CH:33][C:23]3[NH:24][C:25]([CH2:27][NH:28][C:29](=O)[CH2:30][CH3:31])=[N:26][C:22]=3[CH:21]=2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)([CH3:9])[CH3:8].O>C1COCC1>[CH:7]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([NH:19][C:20]2[CH:34]=[CH:33][C:23]3[NH:24][C:25]([CH2:27][NH:28][CH2:29][CH2:30][CH3:31])=[N:26][C:22]=3[CH:21]=2)(=[O:17])=[O:18])=[CH:14][CH:15]=1)([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178460133HCID 178460133, compound

Product 1

HCID 178457108HCID 178457108, compoundYield 3.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium-aluminiumhydride (180 mg, 4.79 mmol) in THF (5 ml, dried Al2O3) at −5-0° C. a solution of N-[5-(4-isopropyl-benzenesulfonylamino)-1H-benzoimidazol-2-ylmethyl]-propionamide (320 mg, 0.80 mmol) in THF (5 ml) was added. After complete addition the mixture was allowed to warm to room temperature and was heated to reflux for 2 h. At 0° C. THF and then water were added. The mixture was dried with Na2SO4. The filtered solution was evaporated in vacuo and the residue was purified by preparative HPLC (water/5% acetonitrile/0.1% acetic acid) to give the product as a yellow oil (10 mg, 3%).

Workup

  1. additionwas added
  2. additionAfter complete addition the mixture
  3. temperaturewas heated
  4. temperatureto reflux for 2 h
  5. customAt 0° C
  6. dry with materialThe mixture was dried with Na2SO4
  7. customThe filtered solution was evaporated in vacuo
  8. customthe residue was purified by preparative HPLC (water/5% acetonitrile/0.1% acetic acid)

Sources & evidence

ORD record
ord-a904c87a3a65496b885a8787e661bf1c
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

Loading…