HCID 69417514, compound → HCID 21073885, compound

HRID 1373582Notes

Reaction equation

HRID 1373582 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][C:20]3[N:29]=[C:28]4[C:23]([CH2:24][CH2:25][C:26](=[O:30])[NH:27]4)=[CH:22][CH:21]=3)[CH2:11][CH2:10]2)[CH:3]=1>CCO.[Pd]>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[N:29]=[C:28]4[C:23]([CH2:24][CH2:25][C:26](=[O:30])[NH:27]4)=[CH:22][CH:21]=3)[CH2:13][CH2:14]2)[CH:3]=1

Participants

4

Reactant 1

HCID 69417514HCID 69417514, compound

Product 1

HCID 21073885HCID 21073885, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7-{5-[4-(4,6-Dimethyl-pyridin-2-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.54 g, 1.33 mmol) was hydrogenated using 20% Pd/C in EtOH for 58 h. The reaction was filtered and concentrated. Purification by liquid chromatography (Biotage 12 SiO2 column, CHCl3 to 1% MeOH/CHCl3) followed by recrystallization from Et2O/hexanes gave the title compound as an off-white solid (313 mg, 0.761 mmol, 57%). MS: APCI: M+1: 408.2 (Exact Mass: 407.27).

Workup

  1. customfor 58 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customPurification by liquid chromatography (Biotage 12 SiO2 column, CHCl3 to 1% MeOH/CHCl3)
  5. customfollowed by recrystallization from Et2O/hexanes

Sources & evidence

ORD record
ord-9834bb8b081341b3a86565ba90f38237
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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