HCID 69419793, compound → HCID 21073876, compound

HRID 1373631Notes

Reaction equation

HRID 1373631 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]=[CH:28][C:27]3[C:26]([CH3:31])([CH3:30])[O:25][C:24](=[O:32])[NH:23][C:22]=3[CH:21]=2)[CH2:11][CH2:10]1>CCO.C1COCC1.CCOC(C)=O.[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]=[CH:28][C:27]3[C:26]([CH3:30])([CH3:31])[O:25][C:24](=[O:32])[NH:23][C:22]=3[CH:21]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 69419793HCID 69419793, compound

Product 1

HCID 21073876HCID 21073876, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

7-{5-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-4,4-dimethyl-1,4-dihydro-pyrido[4,3-d][1,3]oxazin-2-one (452 mg, 0.95 mmol) was hydrogentated using Ra—Ni in EtOH/THF. The reaction was filtered and concentrated. Purification by liquid chromatography (5% MeOH/CH2Cl2 with 0.5% NH4OH) gave a white foam (385 mg, 85% pure). The foam was dissolved in a minimal amount of EtOAc and, upon standing, a white precipitate formed. The precipitate was filtered and washed with Et2O to give the title compound as a white solid (200 mg, 0.42 mmol, 44%). MS: APCI: M+1: 477.1 (Exact Mass: 476.17).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customPurification by liquid chromatography (5% MeOH/CH2Cl2 with 0.5% NH4OH)
  4. customgave a white foam (385 mg, 85% pure)
  5. customa white precipitate formed
  6. filtrationThe precipitate was filtered
  7. washwashed with Et2O

Sources & evidence

ORD record
ord-8f6e1adfc576425fb79db7ad7a30fbdc
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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