HCID 86617474, compound → HCID 86075006, compound

HRID 1162819Notes

Reaction equation

HRID 1162819 reaction equation
[CH3:1][N:2]([CH3:31])[C:3](=[O:30])[CH2:4][CH:5]1[CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8][C:7](=[O:21])[N:6]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1>[Pd].C(O)C>[CH3:31][N:2]([CH3:1])[C:3](=[O:30])[CH2:4][CH:5]1[CH2:10][NH:9][CH2:8][C:7](=[O:21])[N:6]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 86617474HCID 86617474, compound

Product 1

HCID 86075006HCID 86075006, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of N,N-dimethyl [1-(4-fluorobenzyl)-4-(benzyloxycarbonyl)-6-oxo-piperazin-2-yl]acetamide (0.5 g, 1.17 mmol) and 10% palladium on carbon (120 mg; 0.11 mmol) in ethanol (25 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature overnight. The reaction mixture was filtered through a pad of Celite, and concentrated under vacuum to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 7.24-7.28 (m, 2H), 7.01 (t, J=8.6 Hz, 2H), 5.06 (d, J=14.8 Hz, 1H), 4.06 (d, J=14.8 Hz, 1H), 3.87-3.94 (m, 1H), 3.57-3.69 (m, 2H), 2.88-3.08 (m, 9H), 2.48 (d, J=16.3 Hz, 1H). ES MS (M+1)=294.3

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d252db9235fe426db5b3e645cd28655f
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

Loading…