HCID 67050910, compound → HCID 57545338, compound

HRID 598271Notes

Reaction equation

HRID 598271 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N+:24]([O-])=O)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:27])[C:7]=2[N:6]=[C:5]1[CH2:28][CH2:29][CH3:30].CC(C)CN1C2C3C=CC(OC4C=CC([N+]([O-])=O)=CC=4)=CC=3N=C(N)C=2N=C1CCC>>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:4]([CH2:3][CH:2]([CH3:31])[CH3:1])[C:5]([CH2:28][CH2:29][CH3:30])=[N:6][C:7]=3[C:8]([NH2:27])=[N:9][C:10]=2[CH:11]=1

Participants

3

Reactant 2

HCID 67050910HCID 67050910, compoundHCID 67050947HCID 67050947, compound

Product 1

HCID 57545338HCID 57545338, compound

Procedure

A modification of the general method described in Example 41 was followed using 1-(2-methylpropyl)-7-(2-nitrophenoxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine, prepared as described in Example 36, in lieu of 1-(2-methylpropyl)-7-(4-nitrophenoxy)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine. When the reaction was complete, the reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol and methanol:dichloromethane. Following treatment with the ion exchange resin, the crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 98:2 to 94:6). The white, waxy solid was recrystallized from acetonitrile to yield 0.150 g of 7-(2-aminophenoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as tan crystals, mp 197-199° C.

Workup

  1. customprepared
  2. filtrationthe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with methanol and methanol
  5. customthe crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 98:2 to 94:6)
  6. customThe white, waxy solid was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dbf170f9a3b54f0b9d0968b5c7ed7f24
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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