Sodium Hydroxide → 1-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol

HRID 2383122Notes

Reaction equation

HRID 2383122 reaction equation
Cl.C([O:5][CH2:6][C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[NH:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])=[CH:17][CH:16]=[C:15]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH:14]=2)=O)(=O)C.[OH-].[Na+]>CO.O>[CH2:27]([O:26][C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[N:20]([CH2:21][C:22]([CH3:24])([OH:25])[CH3:23])[C:7]([CH2:6][OH:5])=[N:9][C:10]=3[CH:11]=[N:12][C:13]=2[CH:14]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 670510132-({7-Benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride

Product 1

HCID 670509421-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-olYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2-({7-benzyloxy-4-[(2-hydroxy-2-methylpropyl)amino]quinolin-3-yl}amino)-2-oxoethyl acetate hydrochloride (54.0 g, 0.114 mol) in methanol (270 mL) was heated to 55° C., at which point a solution was obtained. A solution of sodium hydroxide (9.2 g, 0.23 mol) in water (90 mL) was then added over a period of five minutes while heating the reaction mixture at reflux. Following the addition, the addition funnel was rinsed with water (10 mL), and the reaction mixture was heated at reflux for one hour. The reaction mixture was then cooled to ˜0° C., and the solid product was isolated by filtration, washed with methanol, deionized water, and a small volume of acetone, and dried under vacuum at 50° C. to provide 42.1 g of 1-[7-benzyloxy-2-(hydroxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol as an off-white solid.

Workup

  1. customwas obtained
  2. temperaturewhile heating the reaction mixture
  3. temperatureat reflux
  4. additionthe addition
  5. washthe addition funnel was rinsed with water (10 mL)
  6. temperaturethe reaction mixture was heated
  7. temperatureat reflux for one hour
  8. temperatureThe reaction mixture was then cooled to ˜0° C.
  9. customthe solid product was isolated by filtration
  10. washwashed with methanol
  11. dry with materiala small volume of acetone, and dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-1fcdd802969b4735b3c25ad822d006d1
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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