HCID 67539123, compound → HCID 46870400, compound

HRID 1400219Notes

Reaction equation

HRID 1400219 reaction equation
[NH2:1][C:2](=[O:33])[CH:3]([OH:32])[CH:4]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[C:20]1[NH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][N:24]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CS(C)=O>[NH2:1][C:2](=[O:33])[C:3](=[O:32])[CH:4]([NH:12][C:13](=[O:31])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[C:20]1[NH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][N:24]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 67539123HCID 67539123, compound

Product 1

HCID 46870400HCID 46870400, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(5-phenyl-1H-imidazol-2-yl)nicotinamide (60 mg, 0.136 mmol) in a mixture of 2 ml of DMSO and 10 ml of dichloromethane IBX-polystyrene was added (371 mg, 0.408 mmol), and the reaction mixture stirred for 16 hours at room temperature. The polymer was filtered off, washed with dichloromethane, the combined organic layers washed with water, dried and evaporated to dryness. The remaining oily residue was treated with water to give a yellow solid which was filtered off and dried again. To a solution of the obtained solid in 20 ml of ethylacetate (EtOAc) two drops of 4N HCl in dioxane were added, and the resulting precipitate filtered off. Recrystallisation of the crude product from 15 ml of ethylacetate yielded 31 mg of the title compound as solid.

Workup

  1. additionwas added (371 mg, 0.408 mmol)
  2. filtrationThe polymer was filtered off
  3. washwashed with dichloromethane
  4. washthe combined organic layers washed with water
  5. customdried
  6. customevaporated to dryness
  7. additionThe remaining oily residue was treated with water
  8. customto give a yellow solid which
  9. filtrationwas filtered off
  10. customdried again
  11. additionTo a solution of the obtained solid in 20 ml of ethylacetate (EtOAc) two drops of 4N HCl in dioxane were added
  12. filtrationthe resulting precipitate filtered off
  13. customRecrystallisation of the crude product from 15 ml of ethylacetate

Sources & evidence

ORD record
ord-1dcebdca6014452d90356ac06e2e07c3
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

Loading…