4-Toluenesulfonyl chloride → [4-amino-7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

HRID 2383125Notes

Reaction equation

HRID 2383125 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:8]2[C:17]3[CH:16]=[CH:15][C:14]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][C:12]=3[N+:11]([O-])=[CH:10][C:9]=2[N:27]=1)(=[O:3])[CH3:2].[OH-].[NH4+:34].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[C:1]([O:4][CH2:5][C:6]1[N:7]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[C:8]2[C:17]3[CH:16]=[CH:15][C:14]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:13][C:12]=3[N:11]=[C:10]([NH2:34])[C:9]=2[N:27]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67050977[7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

Product 1

HCID 67050938[4-amino-7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of [7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-5-oxido-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate (40.0 g, 0.0918 mol) in dichloromethane (650 mL) was cooled to 0° C.; ammonium hydroxide (250 mL of 28%) was added. A solution of p-toluenesulfonyl chloride (29.1 g, 0.153 mol) in dichloromethane (200 mL) was added over a period of 12 minutes while maintaining the reaction temperature below 5.5° C. The reaction mixture was then allowed to warm to room temperature and stirred for one hour. The reaction mixture was diluted with dichloromethane (100 mL), and the organic layer was washed with deionized water (2×400 mL), dried over magnesium sulfate, and filtered. The solution was then treated with activated charcoal for one hour, filtered through a layer of CELITE filter aid, concentrated under reduced pressure, and further dried under vacuum at 60° C. to provide 40.1 g of [4-amino-7-benzyloxy-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-2-yl]methyl acetate.

Workup

  1. temperaturewhile maintaining the reaction temperature below 5.5° C
  2. washthe organic layer was washed with deionized water (2×400 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. additionThe solution was then treated with activated charcoal for one hour
  6. filtrationfiltered through a layer of CELITE
  7. filtrationfilter aid
  8. concentrationconcentrated under reduced pressure
  9. customfurther dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-06c3a14591954c7bb89b1af24b5f8bea
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

Loading…