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

HRID 2120789Notes

Reaction equation

HRID 2120789 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[N:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].[H][H].FC(F)(F)C(O)=[O:28]>[Pt]=O>[OH2:28].[CH2:1]([C:5]1[N:6]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].[CH2:1]([C:5]1[N:6]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:7]2[C:16]3[CH2:15][CH2:14][CH2:13][NH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 103083912-Butyl-1-(2-methylpropyl)imidazo[4,5-c][1,8]naphthyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 686099292-butyl-6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,8]naphthyridin-4-amine hemihydrate

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A catalytic amount of platinum oxide was added to a solution of 2-butyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,8]naphthyridin-4-amine (2.0 g, 6.2 mmole) in trifluoroacetic acid (30 mL). The reaction mixture was reduced on a Parr apparatus under 50 psi (3.5 Kg/cm2) hydrogen pressure. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under vacuum. The residue was combined with water, sodium bicarbonate and 10% sodium hydroxide. An oil was recovered and purified using reverse phase high performance liquid chromatography eluting with 30:70 buffer (7.68 g potassium phosphate, monobasic; 1.69 g of sodium hydroxide, 1 L of water):methanol to provide 2-butyl-6,7,8,9-tetrahydro-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,8]naphthyridin-4-amine hemihydrate as a solid, m.p. 81-84° C. Calculated for C17H27N5+½H2O: %C, 65.77; %H, 9.09; %N, 22.56. Found: %C, 65.57; %H, 9.15; %N, 22.53.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under vacuum
  4. customAn oil was recovered
  5. custompurified
  6. washeluting with 30:70 buffer (7.68 g potassium phosphate, monobasic; 1.69 g of sodium hydroxide, 1 L of water)

Sources & evidence

ORD record
ord-db566f9090b04f3a9498391b7e76df8c
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

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