7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol

HRID 540839Notes

Reaction equation

HRID 540839 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:20]([CH2:26][CH3:27])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.C(OC1C=CC2C3N(CC(C)C)C(CCC)=NC=3C(N)=NC=2C=1)C1C=CC=CC=1>>[CH2:26]([C:20]1[N:21]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:13]2[C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=3[N:16]=[CH:15][C:14]=2[N:19]=1)[CH3:27]

Participants

3

Reactant 2

HCID 113612427-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 670509537-benzyloxy-2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 1363478472-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-olYield 35.8%

Procedure

The general method described in Part J of Example 1 was followed using 7-benzyloxy-2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (3.43 g, 9.54 mmol) in lieu of 7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine. The crude product was recrystallized from acetonitrile, isolated by filtration, and dried for two days in an oven at 60° C. to provide 0.92 g of 2-ethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol as an off-white solid, mp >250° C.

Workup

  1. customThe crude product was recrystallized from acetonitrile
  2. customisolated by filtration
  3. customdried for two days in an oven at 60° C.

Sources & evidence

ORD record
ord-e009677aff744c4fb3cd57954e431c4f
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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