HCID 69088140, compound → HCID 54238815, compound

HRID 1432936Notes

Reaction equation

HRID 1432936 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][NH:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][C:21]=2[CH3:26])[C:13](=[O:27])[CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:26][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][C:20]=1[NH:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][C:13]1=[O:27]

Participants

4

Reactant 1

HCID 69088140HCID 69088140, compound

Product 1

HCID 54238815HCID 54238815, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

4-[2-(3-Methylpyridin-4-ylamino)-ethyl]-3-oxo-piperazine-1-carboxlic acid benzyl ester (0.20 g, 0.54 mmol) is dissolved in anhydrous ethanol (20 mL) and hydrogenated at 50 PSI with 10% Pd/C overnight. After filtration, the filtrate is concentrated. The residue is treated with Pd black in 5% HCO2H/CH2Cl2 (10 ml) for 10 minutes. Filtration and concentration gives crude residue, which is purified by chromatography using NH4OH/MeOH/CH2Cl2 (1:5:95) to give the title compound as a clear syrup (0.078 g, 0.33 mmol). 1H NMR (CDCl3, 300 MHz) δ8.17 (d, 1H), 8.03 (s, 1H), 7.35 (s, 5H), 6.36 (d, 1H), 5.30 (b, 1H), 3.74 (t, 2H), 3.53 (s, 2H), 3.38 (m, 4H), 3.08 (t, 2H), 2.02 (s, 3H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is treated with Pd black in 5% HCO2H/CH2Cl2 (10 ml) for 10 minutes
  4. filtrationFiltration and concentration
  5. customgives crude residue, which
  6. customis purified by chromatography

Sources & evidence

ORD record
ord-b3fce671fb514a61b0dbd86ab00dfc37
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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