HCID 69420265, compound → HCID 21073869, compound

HRID 1373584Notes

Reaction equation

HRID 1373584 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]=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>[Ni].CO>[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]=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 69420265HCID 69420265, compound

Product 1

HCID 21073869HCID 21073869, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

7-{5-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-1H-[1,8]naphthyridin-2-one (160 mg, 0.361 mmol) was hydrogenated using Raney Nickel (0.2 g) in MeOH for 42 h. The reaction was filtered and concentrated. Purification by liquid chromatography (5% MeOH/CH2Cl2 with 1% NH4OH) gave the title compound as a white foam (109 mg, 0.245 mmol, 68%), which was further purified by HPLC to remove a small amount of over-reduced side-product. MS: APCI: M−1: 443.1 (Exact Mass: 444.15).

Workup

  1. customfor 42 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by liquid chromatography (5% MeOH/CH2Cl2 with 1% NH4OH)

Sources & evidence

ORD record
ord-597c21bb125547fcb44af3c78bd26a4d
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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