Cesium carbonate → HCID 67050932, compound

HRID 2383092Notes

Reaction equation

HRID 2383092 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:19][O:20][CH2:21][CH3:22])[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:23])=[CH:5][C:4]=2[N:3]=1.[CH3:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O>CN(C=O)C>[CH2:21]([O:20][CH2:19][C:13]1[N:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([O:23][CH2:24][C:25]4[CH:32]=[CH:31][CH:30]=[C:27]([CH3:28])[CH:26]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:22]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 12099m-Xylyl bromideHCID 13387N-methyl-2-pyrrolidoneHCID 135409766HCID 135409766, compound

Product 1

HCID 67050932HCID 67050932, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The general method described for Examples 22-32 was followed using the following modifications. 4-Amino-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (310 mg, 0.97 mmol) was dissolved in DMF (15 mL) with heating but precipitated from the solution as it cooled to room temperature. A solution of 3-methylbenzyl bromide (197 mg, 1.07 mmol) in DMF (0.5 mL) was added followed by solid cesium carbonate (643 mg, 1.97 mmol). N-Methylpyrrolidone (1 mL) was added to the reaction, and the reaction was stirred overnight. The crude product was purified by column chromatography on silica gel (eluting with chloroform:methanol), triturated with acetonitrile, and isolated by filtration to provide 175 mg of 2-ethoxymethyl-7-(3-methylbenzyloxy)-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 207.0-208.0° C.

Workup

  1. temperaturewith heating
  2. customprecipitated from the solution as it
  3. customThe crude product was purified by column chromatography on silica gel (eluting with chloroform:methanol)
  4. customtriturated with acetonitrile
  5. customisolated by filtration

Sources & evidence

ORD record
ord-5fff6a7d869d4b848d136ff04fd8e87c
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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