HCID 69419367, compound → HCID 21073874, compound

HRID 1373591Notes

Reaction equation

HRID 1373591 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]([CH:24]=[C:25]([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>C1COCC1.CCO.[Ni]>[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]([CH:24]=[C:25]([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 69419367HCID 69419367, compound

Product 1

HCID 21073874HCID 21073874, compoundYield 51.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-{5-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3-methyl-1H-[1,8]naphthyridin-2-one (0.43 g, 0.94 mmol) in THF was added to a slurry of Raney Ni in EtOH. The mixture was hydrogentated for 4 h at 40 psi. The reaction mixture was filtered through a small celite bed and rinsed with CH2Cl2 and mMeOH. The filtrate was concentrated and purified by column chromatography on silica (10% MeOH/EtOAc) to afford the title compound as a pale yellow solid (0.22 g, 51.4%). mp: 157–158° C.; 1H NMR (400 MHz, CDCl3) δ 9.00 (br s, 1H), 7.75 (d, 1H), 7.50 (s, 1H), 7.15 (m, 2H), 7.00–6.90 (m, 2H), 3.10 (br s, 4H), 2.80 (t, 2H), 2.60 (br s, 4H), 2.42–2.38 (m, 2H), 2.20 (s, 3H), 1.82–1.80 (m, 2H), 1.70–1.60 (m, 4H); MS: ES+: 459.01 (M+H)+, 460.97 (Exact mass: 458.16).

Workup

  1. filtrationThe reaction mixture was filtered through a small celite bed
  2. washrinsed with CH2Cl2 and mMeOH
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography on silica (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-50419e8e7b754a2f8b4ff05a6a9de16f
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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