Dichloromethane → HCID 57380087, compound

HRID 2174668Notes

Reaction equation

HRID 2174668 reaction equation
[CH:1]1([NH:4][C:5](=[O:34])[CH:6]([OH:33])[CH:7]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]=2[N:23]2[CH:31]=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[N:24]2)[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.ClCCl>>[CH:1]1([NH:4][C:5](=[O:34])[C:6](=[O:33])[CH:7]([NH:15][C:16](=[O:32])[C:17]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]=2[N:23]2[CH:31]=[C:30]3[C:25]([CH:26]=[CH:27][CH:28]=[CH:29]3)=[N:24]2)[CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 67958397HCID 67958397, compound

Product 1

HCID 57380087HCID 57380087, compoundYield 60.5%

Procedure

To a solution of N-[4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl]-2-(2H-indazol-2-yl)nicotinamide (116 mg, 0.255 mmol) in dichloromethane (30 ml) Dess-Martin periodinane (commercial solution of 15% by weight in dichloromethane; 1 ml, 0.460 mmol) was added and the mixture stirred for 5 minutes. The reaction was then quenched by adding a saturated aqueous solution of sodium hydrogen carbonate (NaHCO3) and water (25 ml each). Afterwards the organic layer was washed twice with water, dried over magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The obtained residue was treated with n-pentane (100 ml), filtered off and then refluxed in a mixture of methyl-tert.-butylether (15 ml) and a 4 N solution of HCl in dioxane (50 μl). After stirring for 2 hr at room temperature the solid was filtered off under suction and recrystallized from isopropanol to give 70 mg of the title compound as a white solid.

Workup

  1. customThe reaction was then quenched
  2. additionby adding a saturated aqueous solution of sodium hydrogen carbonate (NaHCO3) and water (25 ml each)
  3. washAfterwards the organic layer was washed twice with water
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionThe obtained residue was treated with n-pentane (100 ml)
  8. filtrationfiltered off
  9. temperaturerefluxed in a mixture of methyl-tert.-butylether (15 ml)
  10. stirringAfter stirring for 2 hr at room temperature the solid
  11. filtrationwas filtered off under suction
  12. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-443d96693e904b619fb528b9853b35af
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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