Ammonium Hydroxide → 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9400Notes

Reaction equation

HRID 9400 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:29][O:30][CH2:31][CH3:32])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:5][C:4]=2[N:3]=1.[OH-].[NH4+]>O>[CH2:31]([O:30][CH2:29][C:13]1[N:14]([CH2:15][CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:32]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21984025tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

Product 1

HCID 100474812-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amineYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (0.64 g) was deprotected according to the method described in Example 177. The crude solid was dissolved in water (10 mL), and ammonium hydroxide was added until the solution was basic. The mixture was then extracted with chloroform (2×10 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from acetonitrile and dried for 16 hours in a vacuum oven at 60° C. to provide 0.28 g of 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white, crystalline solid, mp 142–143° C.

Workup

  1. extractionThe mixture was then extracted with chloroform (2×10 mL)
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from acetonitrile
  6. customdried for 16 hours in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-c56825bcfe01483a83fa38235d7cbd81
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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