Trichloroacetyl isocyanate → 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2383139Notes

Reaction equation

HRID 2383139 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N+:15]([O-])=[CH:14][C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:31]=C=O)=O.C[O-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:31])[C:13]3[N:20]=[CH:21][N:22]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:12]=3[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 76400Trichloroacetyl isocyanate2×HCID 10942334Sodium MethoxideHCID 670510288-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline

Product 1

HCID 575453368-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine

Procedure

A modification of the general method described in Part C of Example 3 was followed using 8-benzyloxy-1-(2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinoline (2.0 g, 5.8 mmol) as the starting material. The reaction with trichloroacetyl isocyanate was not complete after one hour as evidenced by a TLC analysis. Additional trichloroacetyl isocyanate (0.1 equivalent) was added, and the reaction was stirred for an additional hour. Following the reaction with sodium methoxide, the solid product was isolated by filtration and recrystallized from ethanol. The crystals were dried overnight in a vacuum oven at 45° C. to provide 1.6 g of 8-benzyloxy-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 214-216° C.

Workup

  1. customthe solid product was isolated by filtration
  2. customrecrystallized from ethanol
  3. customThe crystals were dried overnight in a vacuum oven at 45° C.

Sources & evidence

ORD record
ord-cdeba2a6568c48419974c845466aa849
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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