HCID 69422419, compound → HCID 21073873, compound

HRID 1373594Notes

Reaction equation

HRID 1373594 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]([C:24]([CH3:32])=[C:25]([CH3:31])[C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>C1COCC1.C(O)C.[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]([C:24]([CH3:32])=[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 69422419HCID 69422419, compound

Product 1

HCID 21073873HCID 21073873, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-{5-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3,4-dimethyl-1H-[1,8]naphthyridin-2-one (80 mg, 0.17 mmol) was dissolved in a minimal amount of THF (2 mL) and the solution was diluted with ethanol (10 mL). The solution was treated with Raney Nickel (0.5 mL slurry in water) and shaken under 45 psi H2 for 3 h. The mixture was filtered through celite. The celite pad was washed with THF (2×10 mL), and the filtrate was evaporated in vacuo. The crude solid was purified by column chromatography (5% MeOH/CH2Cl2) to yield the title compound as a white solid (64 mg, 80%). mp 202–203° C., 1H NMR (400 MHz, CDCl3) δ 8.98 (br s, 1H) 7.84 (d, 1H), 7.20–7.15 (m, 2H), 7.04 (d, 1H), 6.98–6.95 (m, 1H), 3.15–3.00 (m, 4H), 2.81 (t, 2H), 2.70–2.55 (m, 4H), 2.46–2.36 (m, 5H), 2.22 (s, 3H), 1.82–1.75 (m, 2H), 1.60–1.50 (m, 2H), 1.45–1.36 (m, 2H), MS ES+ 473.00 (M+H)+ (Exact Mass: 472.18).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washThe celite pad was washed with THF (2×10 mL)
  3. customthe filtrate was evaporated in vacuo
  4. customThe crude solid was purified by column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-45a077cfcf314e70a71b12a56cf1a835
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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