HCID 11779269, compound → HCID 15224402, compound

HRID 991890Notes

Reaction equation

HRID 991890 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-e212ac82da024312a8bfabcf951a104c
Source dataset
uspto-grants-2002_10
Patent number
US06465654B2

Reaction notes

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