HCID 69421276, compound → HCID 21073893, compound

HRID 1373579Notes

Reaction equation

HRID 1373579 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]=[CH:18][C:19]3[N:28]=[C:27]4[C:22]([CH2:23][CH2:24][C:25](=[O:29])[NH:26]4)=[CH:21][CH:20]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1>CCO.[Pd]>[CH3:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]3[N:28]=[C:27]4[C:22]([CH2:23][CH2:24][C:25](=[O:29])[NH:26]4)=[CH:21][CH:20]=3)[CH2:12][CH2:13]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69421276HCID 69421276, compound

Product 1

HCID 21073893HCID 21073893, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-{5-[4-(6-Methyl-pyridin-2-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.343 g, 0.876 mmol) was hydrogenated using 20% Pd/C in EtOH for 103 h. The reaction was filtered and concentrated. Purification by liquid chromatography (Biotage 12 SiO2 column, CH2Cl2 to 1% MeOH/CH2Cl2) followed by recrystallization from Et2O gave the title compound as a white powder (42 mg, 0.01 mmol, 12%). MS: APCI: M+1: 394.2 (Exact Mass: 393.25).

Workup

  1. customfor 103 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by liquid chromatography (Biotage 12 SiO2 column, CH2Cl2 to 1% MeOH/CH2Cl2)
  5. customfollowed by recrystallization from Et2O

Sources & evidence

ORD record
ord-e4d94e35eacd42c3931da658a99e58f8
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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