Diethyl Ether → HCID 21073883, compound

HRID 1373577Notes

Reaction equation

HRID 1373577 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[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.CCOCC>C1COCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][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)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 69417476HCID 69417476, compound

Product 1

HCID 21073883HCID 21073883, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7-{5-[4-(2-Chloro-4-fluoro-phenyl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.268 g, 0.623 mmol) was hydrogenated using Ra—Ni (0.2 g) in THF for 13 hours. The reaction was filtered and concentrated to give an oil. Et2O was added and the product crashed out. The mixture was filtered and dried to give the title compound as a white solid (0.214 g, 80%). MS: APCI: M+1: 431.3 (Exact Mass: 430.19).

Workup

  1. customfor 13 hours
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customto give an oil
  5. filtrationThe mixture was filtered
  6. customdried

Sources & evidence

ORD record
ord-8cc4740b424045e184b78af02216c024
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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