HCID 11779269, compound → HCID 15224402, compound

HRID 1601666Notes

Reaction equation

HRID 1601666 reaction equation
[N:1]([CH2:4][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]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:17][C:9]1[C:8]2[N:18]=[C:5]([CH2:4][NH2:1])[N:6]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

5

Reactant 2

HCID 11779269HCID 11779269, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15224402HCID 15224402, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Azidomethyl-1(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.2 g, 0.0108 mol, Example 11) was added to ethanol (300 mL) and 5% Pd/C (about 1 g) was added to the mixture. The mixture was hydrogenated on a Parr apparatus until hydrogen uptake stopped. Hydrogen was removed and the mixture was flushed with hydrogen to regenerate the catalyst. Hydrogenation was resumed. This procedure was repeated until no more hydrogen was absorbed. The catalyst was filtered from the mixture and the filtrate was evaporated. The residue was recrystallized several times from ethanol to give yellowish crystals m.p. 287-291° C. Analysis: Calculated: C, 66.9; H, 7.1; N, 26.0. Found: C, 66.5; H, 7.2; N, 25.1.

Workup

  1. additionwas added to the mixture
  2. customHydrogen was removed
  3. customthe mixture was flushed with hydrogen
  4. customwas absorbed
  5. filtrationThe catalyst was filtered from the mixture
  6. customthe filtrate was evaporated
  7. customThe residue was recrystallized several times from ethanol

Sources & evidence

ORD record
ord-c0af5f030e4b447f877868ff31290237
Source dataset
uspto-grants-1999_11
Patent number
US05977366

Reaction notes

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