1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine → 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine

HRID 2244715Notes

Reaction equation

HRID 2244715 reaction equation
[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][N:12]=[CH:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1.[H][H]>FC(F)(F)C(O)=O.[Pt]=O>[CH3:1][CH:2]([CH3:18])[CH2:3][N:4]1[C:16]2[C:15]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[N:9]=[C:8]([NH2:17])[C:7]=2[N:6]=[CH:5]1

Participants

5

Reactant 2

HCID 120158061-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 120158076,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amineYield 0.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A catalytic amount of platinum oxide was added to a solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine (0.4 g, 1.66 mol)) in trifluoroacetic acid. The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen pressure overnight. The reaction mixture was filtered and washed with methanol to remove the catalyst. The filtrate was concentrated under vacuum. The residue was combined with dichloromethane and aqueous sodium bicarbonate was added until the mixture was basic. The dichloromethane layer was separated. The aqueous layer was extracted five times with dichloromethane (100 mL). The dichloromethane extracts were combined, dried over magnesium sulfate and concentrated under vacuum. The resulting residue was recrystallized from toluene to provide 0.34 g of 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,7]naphthyridin-4-amine as a solid, m.p. 220-223° C. Analysis: Calculated for C13H19N5+¼H2O: % C, 62.50% H, 7.87; % N, 28.03; Found: % C, 62.50; % H, 7.72; % N, 27.46.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated under vacuum
  5. additionwas added until the mixture
  6. customThe dichloromethane layer was separated
  7. extractionThe aqueous layer was extracted five times with dichloromethane (100 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe resulting residue was recrystallized from toluene

Sources & evidence

ORD record
ord-759baaab90d7461d92ab40988bd1d097
Source dataset
uspto-grants-2010_03
Patent number
US07678918B2

Reaction notes

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