Cesium carbonate → HCID 57545298, compound

HRID 2383151Notes

Reaction equation

HRID 2383151 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.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Cl>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][CH2:30][C:31]4[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=4[CH3:33])=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11093alpha-Chloro-o-xyleneHCID 135409766HCID 135409766, compound

Product 1

HCID 57545298HCID 57545298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Amino-2-ethoxymethyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-ol (750 mg, 2.39 mmol) was dissolved with heating in DMF (50 mL). Solid cesium carbonate (1.55 g, 4.77 mmol) was added. After 15 minutes, 2-methylbenzyl chloride (487 mg, 2.63 mmol) was added to the mixture. The reaction was stirred overnight at ambient temperature, then was poured onto water (500-750 mL) and a milky white precipitate formed immediately. The mixture was stirred for 1 hour, and then the precipitate was isolated by filtration. The solid was purified by flash chromatography (silica gel, gradient elution with 0.5-2% methanol in chloroform) followed by recrystallization from 2-propanol. The final product was isolated by filtration and dried overnight under vacuum at 60° C. to provide 780 mg of 2-(ethoxymethyl)-7-[(2-methylbenzyl)oxy]-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off white solid, mp 216.0-218.0° C.

Workup

  1. additionwas poured onto water (500-750 mL)
  2. customa milky white precipitate formed immediately
  3. stirringThe mixture was stirred for 1 hour
  4. customthe precipitate was isolated by filtration
  5. customThe solid was purified by flash chromatography (silica gel, gradient elution with 0.5-2% methanol in chloroform)
  6. customfollowed by recrystallization from 2-propanol

Sources & evidence

ORD record
ord-bace35a74ea949db8a5a136ea5cdba78
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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