HCID 69419271, compound → HCID 21073881, compound

HRID 1373578Notes

Reaction equation

HRID 1373578 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][C:21]2[N:30]=[C:29]3[C:24]([CH2:25][CH2:26][C:27](=[O:31])[NH:28]3)=[CH:23][CH:22]=2)[CH2:12][CH2:11]1>[Ni].CCO.C1COCC1>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[N:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[N:30]=[C:29]3[C:24]([CH2:25][CH2:26][C:27](=[O:31])[NH:28]3)=[CH:23][CH:22]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 69419271HCID 69419271, compound

Product 1

HCID 21073881HCID 21073881, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

7-{5-[4-(2-Chloro-4-fluoro-3-methyl-phenyl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.382 g, 0.862 mmol) was hydrogenated using Ra—Ni (0.5 g) in 1:1 EtOH/THF (50 mL) for 12 h. The reaction was filtered and concentrated. Purification by liquid chromatography (SiO2, 5% MeOH/CH2Cl2 to 7% MeOH/CH2Cl2) gave the title compound as a light yellow foam (342 mg, 0.769 mmol, 89%). MS: APCI: M+1: 445.2 (Exact Mass: 444.21).

Workup

  1. customfor 12 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by liquid chromatography (SiO2, 5% MeOH/CH2Cl2 to 7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-682b13cee3e04000a81d9e27d5968717
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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