Sodium Chloride → 1-[4-amino-2-(2-methoxyethyl)-7-(5-methylisoxazol-3-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 598357Notes

Reaction equation

HRID 598357 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([OH:24])=[CH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][C:33]1[CH:37]=[C:36]([CH3:38])[O:35][N:34]=1.[Cl-].[Na+]>O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][CH2:21][O:22][CH3:23])[N:14]([CH2:15][C:16]([CH3:18])([OH:19])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([O:24][CH2:32][C:33]3[CH:37]=[C:36]([CH3:38])[O:35][N:34]=3)=[CH:5][C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 27763043-(Bromomethyl)-5-methylisoxazoleHCID 1360752004-amino-1-(2-hydroxy-2-methylpropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 575453101-[4-amino-2-(2-methoxyethyl)-7-(5-methylisoxazol-3-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Amino-1-(2-hydroxy-2-methylpropyl)-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-7-ol was alkylated as described in the general procedure for Examples 7-20, using 2 equivalents of cesium carbonate and 1.1 eq of 3-(bromomethyl)-5-methylisoxazole. After stirring overnight at room temperature, the reaction mixture was poured into 200 mL of water containing 20 g of sodium chloride. The resulting precipitate was filtered, dissolved in dichloromethane, and purified by flash column chromatography on silica gel, eluting with a gradient of 0-8% methanol in dichloromethane. The clean fractions were combined and concentrated. The resulting solid was slurried in cold acetonitrile, filtered, and dried under reduced pressure to yield 315 mg of 1-[4-amino-2-(2-methoxyethyl)-7-(5-methylisoxazol-3-ylmethoxy)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid, mp 169.0-170.0.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. dissolutiondissolved in dichloromethane
  3. custompurified by flash column chromatography on silica gel
  4. washeluting with a gradient of 0-8% methanol in dichloromethane
  5. concentrationconcentrated
  6. filtrationfiltered
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-af0a0230a6f647c89de9fbb75f3aede4
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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