HCID 86722893, compound → HCID 86722892, compound

HRID 624568Notes

Reaction equation

HRID 624568 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:17][CH:18]([NH:21]C(=O)OCC3C=CC=CC=3)[CH2:19][OH:20])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:32])[N:4]([CH3:33])[C:3]1=[O:34].CN1C2=CN(CC3COC(=O)N3)C(C3C=CC=CC=3)=C2C(=O)N(C)C1=O>[Pd].C(O)C>[NH2:21][CH:18]([CH2:19][OH:20])[CH2:17][N:9]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:6]2[C:7]([N:2]([CH3:1])[C:3](=[O:34])[N:4]([CH3:33])[C:5]2=[O:32])=[CH:8]1

Participants

5

Reactant 2

HCID 86722893HCID 86722893, compoundHCID 86722894HCID 86722894, compound

Product 1

HCID 86722892HCID 86722892, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl (1-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-3-hydroxypropan-2-yl)carbamate and 1,3-dimethyl-6-((2-oxooxazolidin-4-yl)methyl)-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (1.67 g) and 10% palladium on carbon (200 mg, 3.61 mmol) were suspended in ethanol (50 ml) and stirred under an atmosphere of hydrogen for 18 hours. The mixture was passed through pre-packed Celite® cartridge (10 g, filter material) and the residue washed with ethanol (20 ml). The combined filtrates were evaporated under vacuum. The residue was suspended in THF (18 ml) and water (5 ml). Lithium hydroxide (20 mg) was added and the mixture stirred at room temperature for 4 hours, then quenched with 2M HCl (aq). NaHCO3(aq) solution (20 ml) was added to achieve pH 6 and the mixture extracted with DCM (3×30 ml), passed through a hydrophobic frit and evaporated under vacuum to afford the title compound.

Workup

  1. filtrationThe mixture was passed through pre-packed Celite® cartridge (10 g, filter material)
  2. washthe residue washed with ethanol (20 ml)
  3. customThe combined filtrates were evaporated under vacuum
  4. additionLithium hydroxide (20 mg) was added
  5. stirringthe mixture stirred at room temperature for 4 hours
  6. customquenched with 2M HCl (aq)
  7. additionNaHCO3(aq) solution (20 ml) was added
  8. extractionthe mixture extracted with DCM (3×30 ml)
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-cca21c5b68484803b0d3026dcdfba606
Source dataset
uspto-grants-2016_04
Patent number
US09303035B2

Reaction notes

Loading…