Hydrochloric Acid → HCID 21073887, compound

HRID 1373576Notes

Reaction equation

HRID 1373576 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[N:31]=[C:30]4[C:25]([CH2:26][CH2:27][C:28](=[O:32])[NH:29]4)=[CH:24][CH:23]=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.Cl>C1COCC1.CCOCC.[Ni]>[C:1]1([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]3[N:31]=[C:30]4[C:25]([CH2:26][CH2:27][C:28](=[O:32])[NH:29]4)=[CH:24][CH:23]=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

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 69420344HCID 69420344, compound

Product 1

HCID 21073887HCID 21073887, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

7-{5-[4-(5,6,7,8-Tetrahydro-naphthalen-1-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.225 g, 0.523 mmol) was hydrogenated using Ra—Ni (0.25 g) in THF for 16 hours. The reaction was filtered and concentrated to give a foam. This was dissolved in Et2O and 1M HCl in Et2O (1 equiv) was added. The precipitate was filtered and dried to give the title compound as a white solid (0.157 g, 70%). MS: APCI: M+1: 433.4 (Exact Mass: 432.29).

Workup

  1. customfor 16 hours
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customto give a foam
  5. filtrationThe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-3d445e8b459b4a78884dd49293bee55c
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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