HCID 69423256, compound → HCID 21073872, compound

HRID 1373574Notes

Reaction equation

HRID 1373574 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][CH2:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>CCO.C1COCC1.[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]([CH2:24][CH2:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 69423256HCID 69423256, compound

Product 1

HCID 21073872HCID 21073872, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

7-{5-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (1.85 g, 4.16 mmol) was hydrogenated using Ra—Ni (1 g) in EtOH/THF (50 mL) for 1.4 h. The reaction was filtered and concentrated to give a solid. Recrystallization from hot CH3CN gave the title compound as a white solid (1.58 g, 3.54 mmol, 85%). MS: APCI: M+1: 447.1 (Exact Mass: 446.16).

Workup

  1. customfor 1.4 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customto give a solid
  5. customRecrystallization from hot CH3CN

Sources & evidence

ORD record
ord-9440aa35f5c44704a00b062fa98458ed
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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