Water → HCID 67023906, compound

HRID 450721Notes

Reaction equation

HRID 450721 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:10][C:11]([C:13]1[NH:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([NH:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1)(=[O:25])=[O:24])=[CH:17][CH:16]=2)=O)[CH2:8][CH3:9].O>O1CCCC1>[CH:32]([C:29]1[CH:28]=[CH:27][C:26]([S:23]([NH:22][C:18]2[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]([CH2:11][NH:10][CH2:7][CH2:8][CH3:9])=[CH:21]3)(=[O:24])=[O:25])=[CH:31][CH:30]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67023878HCID 67023878, compound

Product 1

HCID 67023906HCID 67023906, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of lithium aluminiumhydride (590 mg, 15.54 mmol) in tetrahydrofuran (THF) (40 ml, dried over Al2O3) at −5 to 0° C. a solution of 5-(4-isopropyl-benzenesulfonylamino)-1H-indole-2-carboxylic acid propylamide (1.03 g, 2.59 mmol) in THF (10 ml) was added. After complete addition the mixture was allowed to warm to room temperature and was heated to reflux for 3 h. At 0° C. THF and then water were added. The mixture was dried with Na2SO4. The filtered solution was evaporated and the residue was purified by column chromatography (toluene:THF:methanol, 4:1:1+2.5% triethylamine) to give the product as a yellow powder (240 mg, 24%).

Workup

  1. additionwas added
  2. additionAfter complete addition the mixture
  3. temperaturewas heated
  4. temperatureto reflux for 3 h
  5. customAt 0° C
  6. dry with materialThe mixture was dried with Na2SO4
  7. customThe filtered solution was evaporated
  8. customthe residue was purified by column chromatography (toluene:THF:methanol, 4:1:1+2.5% triethylamine)

Sources & evidence

ORD record
ord-9d232307afc84fef87a53ba27005b819
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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