HCID 69419982, compound → HCID 21073447, compound

HRID 1373622Notes

Reaction equation

HRID 1373622 reaction equation
[C:1]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C:22]3[CH:23]=[CH:24][C:25]4[O:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=4[N:31]=3)[CH2:13][CH2:12]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1>C1COCC1.[Ni]>[C:1]1([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:26][CH2:27][C:28](=[O:32])[NH:29][C:30]=4[N:31]=3)[CH2:15][CH2:16]2)[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 69419982HCID 69419982, compound

Product 1

HCID 21073447HCID 21073447, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6-{5-[4-(5,6,7,8-Tetrahydro-naphthalen-1-yl)-piperazin-1-yl]-pent-1-enyl}-4H-pyrido[3,2-b][1,4]oxazin-3-one (0.098 g, 0.226 mmol) was hydrogenated using Ra—Ni in THF for 16 hours. The reaction was filtered and concentrated to give an oil. Purification by chromatography on silica gel (0–5% MeOH/EtOAc) afforded the title compound as a film (0.059 g, 61%). This was dissolved in Et2O and 1M HCl in Et2O (1 equivalent) was added. The resulting precipitate was filtered and dried to give a white solid. MS: APCI: M+1: 435.5 (Exact Mass: 434.27).

Workup

  1. customfor 16 hours
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customto give an oil
  5. customPurification by chromatography on silica gel (0–5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-a697ccfa75ac4ca7b71379bdc23e19b1
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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