4-Toluenesulfonyl chloride → HCID 58833668, compound

HRID 540896Notes

Reaction equation

HRID 540896 reaction equation
C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH3:12][O:13][CH2:14][CH2:15][C:16]1[N:17]([CH2:42][CH2:43][CH3:44])[C:18]2[C:27]3[CH:26]=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:23][C:22]=3[N+:21]([O-])=[CH:20][C:19]=2[N:41]=1.[OH-].[NH4+:46]>ClCCl>[NH2:46][C:20]1[C:19]2[N:41]=[C:16]([CH2:15][CH2:14][O:13][CH3:12])[N:17]([CH2:42][CH2:43][CH3:44])[C:18]=2[C:27]2[CH:26]=[CH:25][C:24]([O:28][CH2:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:23][C:22]=2[N:21]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 68973550HCID 68973550, compound

Product 1

HCID 58833668HCID 58833668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonyl chloride (8.0 g, 42 mmol) was added over ten minutes to a stirred mixture of tert-butyl 3-{[2-(2-methoxyethyl)-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate (19.3 g, 42.0 mmol) in dichloromethane (300 mL) and concentrated ammonium hydroxide (300 mL) at 7° C. The mixture was allowed to stir for 20 minutes, then the cooling bath was removed and the mixture was allowed to stir at ambient temperature for 2 hours. The layers were separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Recrystallization from acetonitrile afforded 12.0 g of tert-butyl 3-{[4-amino-2-(2-methoxyethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate as flocculent white crystals, mp 133.5-135° C.

Workup

  1. customthe cooling bath was removed
  2. stirringto stir at ambient temperature for 2 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washwashed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-85178f284a3b4d26ad91f9663af13560
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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