4-Toluenesulfonyl chloride → HCID 58833628, compound

HRID 540909Notes

Reaction equation

HRID 540909 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:40][CH2:41][CH3:42])[C:18]2[C:27]3[CH:26]=[C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][C:33]4=[O:37])[CH:24]=[CH:23][C:22]=3[N+:21]([O-])=[CH:20][C:19]=2[N:39]=1)[CH3:13].[OH-].[NH4+:44]>ClCCl>[NH2:44][C:20]1[C:19]2[N:39]=[C:16]([CH2:15][O:14][CH2:12][CH3:13])[N:17]([CH2:40][CH2:41][CH3:42])[C:18]=2[C:27]2[CH:26]=[C:25]([O:28][CH2:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][C:33]3=[O:37])[CH:24]=[CH:23][C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68973272HCID 68973272, compound

Product 1

HCID 58833628HCID 58833628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonyl chloride (0.700 g, 3.66 mmol) was added to a stirred mixture of 1-(3-{[2-(ethoxymethyl)-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}propyl)pyrrolidin-2-one (1.56 g, 3.66 mmol), ammonium hydroxide (24 mL), and dichloromethane (36 mL) at room temperature. After 16 hours, the layers were separated and the aqueous layer was extracted with dichloromethane (3×50 mL). The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Recrystallization from acetonitrile afforded 0.759 g of 1-(3-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}propyl)pyrrolidin-2-one as off-white needles, mp 188.5-190° C.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-02669b31823a40d49da3d80e18480e58
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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