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

HRID 989075Notes

Reaction equation

HRID 989075 reaction equation
CC(C)C[N:4]1[C:8]2=[C:9]3[N:19]=[CH:18][N:17]=[C:10]3[C:11]3[CH:12]=[CH:13][CH:14]=[N:15][C:16]=3[N:7]2N=N1.[H][H]>[Pt]=O.FC(F)(F)C(O)=O.Cl>[CH3:10][CH:11]([CH3:12])[CH2:16][N:17]1[C:10]2[C:11]3[CH2:12][CH2:13][CH2:14][NH:15][C:16]=3[N:7]=[C:8]([NH2:4])[C:9]=2[N:19]=[CH:18]1

Participants

6

Reactant 2

HCID 221727491-(2-methylpropyl)-1H-tetrazolo(1,5-a]imidazo[4,5-c][1,8]naphthyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 120158116,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c](1,8]naphthyridin-4-amine

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 313Hydrochloric AcidSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Platinum oxide catalyst was added to a solution of 1-(2-methylpropyl)-1H-tetrazolo(1,5-a]imidazo[4,5-c][1,8]naphthyridine in trifluoroacetic acid (30 mL). The reaction mixture was reduced on a Parr apparatus at 50 psi (3.5 Kg/cm2) hydrogen pressure for 5 hours. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum. The residue was combined with water and sodium bicarbonate. The resulting precipitate was isolated by filtration. The solid was dissolved in 1N hydrochloric acid and charcoal filtered. The filtrate was treated with 10% sodium hydroxide. The resulting precipitate was isolated by filtration then recrystallized from ethyl acetate/methanol. The recrystallized material was dissolved in dichloromethane/methanol and placed on a silica gel column. The column was eluted with 10% methanol in ethyl acetate. The eluant was concentrated under vacuum and the residue was recrystallized from methanol/water to provide 0.9 g of 6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,8]naphthyridin-4-amine as a solid, m.p. 231-233° C. Analysis: Calculated for C13H19N5: %C, 63.65; %H, 7.81; %N, 28.55; Found: %C, 62.99; %H, 7.74; %N, 28.33.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under vacuum
  4. customThe resulting precipitate was isolated by filtration
  5. filtrationcharcoal filtered
  6. additionThe filtrate was treated with 10% sodium hydroxide
  7. customThe resulting precipitate was isolated by filtration
  8. customthen recrystallized from ethyl acetate/methanol
  9. dissolutionThe recrystallized material was dissolved in dichloromethane/methanol
  10. washThe column was eluted with 10% methanol in ethyl acetate
  11. concentrationThe eluant was concentrated under vacuum
  12. customthe residue was recrystallized from methanol/water

Sources & evidence

ORD record
ord-809281abd05a4b3a8b33120d43199e6a
Source dataset
uspto-grants-2003_10
Patent number
US06638944B2

Reaction notes

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