HCID 86642102, compound → HCID 68596222, compound

HRID 1943202Notes

Reaction equation

HRID 1943202 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6](=[O:12])[N:5]3[CH2:13][C@@H:14]([CH2:15][N:16]4[CH2:21][CH2:20][C:19]([NH:23]C(=O)OCC5C=CC=CC=5)([CH3:22])[CH2:18][CH2:17]4)[N:3]1[C:4]=23.[H][H]>C(O)C.[Pd]>[NH2:23][C:19]1([CH3:22])[CH2:18][CH2:17][N:16]([CH2:15][C@H:14]2[N:3]3[C:4]4[N:5]([C:6](=[O:12])[CH2:7][CH2:8][C:9]=4[CH:10]=[CH:11][C:2]3=[O:1])[CH2:13]2)[CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 86642102HCID 86642102, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 68596222HCID 68596222, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A solution of phenylmethyl (1-{[(2R)-4,9-dioxo-1,2,8,9-tetrahydro-4H,7H-imidazo[1,2,3-ij]-1,8-naphthyridin-2-yl]methyl}-4-methyl-4-piperidinyl)carbamate (1.848 g, 4.10 mmol) in ethanol at rt under argon was treated with palladium on carbon (10% paste) (0.462 g, 4.34 mmol) (20% w/w) and stirred under 1 atmosphere of hydrogen for 2 h, reaction mixture was filtered through a thin pad of Kielselguhr eluting with ethanol (100 ml). The filtrate was treated with palladium on carbon (10% paste) (0.462 g, 4.34 mmol) and stirred under 1 atm of hydrogen for 18 h. The reaction mixture was filtered through a thin pad of Kielselguhr eluting with ethanol (500 ml) and the filtrate was then evaporated to give the product as a yellow solid (1.294 g, 100%).

Workup

  1. customreaction mixture
  2. filtrationwas filtered through a thin pad of Kielselguhr
  3. washeluting with ethanol (100 ml)
  4. filtrationThe reaction mixture was filtered through a thin pad of Kielselguhr
  5. washeluting with ethanol (500 ml)
  6. customthe filtrate was then evaporated

Sources & evidence

ORD record
ord-efbcbfabede7423f9f3fcce8e0953c35
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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