HCID 69419265, compound → HCID 21073870, compound

HRID 1373598Notes

Reaction equation

HRID 1373598 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][C:20]2[N:29]=[C:28]3[C:23]([CH2:24][C:25]([CH3:32])([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>CCOC(C)=O.O=[Pt]=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[N:29]=[C:28]3[C:23]([CH2:24][C:25]([CH3:32])([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 69419265HCID 69419265, compound

Product 1

HCID 21073870HCID 21073870, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A Parr shaker was charged with PtO2 (0.12 g) and EtOAc (25 mL) was added under N2. The catalyst was shaken under a H2 atmosphere (50 psi) for 10 min and a suspension of 7-{5-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3,3-dimethyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.54 g, 1.15 mmol) in EtOAc (125 mL) was added. The mixture was shaken under H2 (50 psi) for 1.5 h. The reaction was filtered through Celite washing with MeOH and the filtrate was concentrated to give an oily residue. Hexanes was added and the mixture was concentrated to give the title compound as a white solid (0.54 g, 99%). MS: ESI: m/z: 475.32 (Exact Mass: 474.20).

Workup

  1. additionwas added under N2
  2. additionwas added
  3. stirringThe mixture was shaken under H2 (50 psi) for 1.5 h
  4. filtrationThe reaction was filtered through Celite
  5. washwashing with MeOH
  6. concentrationthe filtrate was concentrated
  7. customto give an oily residue
  8. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-d1819261f27245388f45377bf5e32fc3
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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