4-Toluenesulfonyl chloride → HCID 57447128, compound

HRID 2366744Notes

Reaction equation

HRID 2366744 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([O:14][CH2:15][C:16]1[N:17]([CH2:29][C:30]2([C:36]([NH2:38])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH3:13].[OH-].[NH4+:40].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:40][C:20]1[C:19]2[N:28]=[C:16]([CH2:15][O:14][CH2:12][CH3:13])[N:17]([CH2:29][C:30]3([C:36]([NH2:38])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:18]=2[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N:21]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69506697HCID 69506697, compound

Product 1

HCID 57447128HCID 57447128, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

mCPBA (953 mg of 77% pure material, 4.25 mmol) was added to a solution of 1-{[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxamide (1.30 g, 3.54 mmol) in chloroform (15 mL); the reaction was stirred for one hour at ambient temperature. Ammonium hydroxide (15 mL) and p-toluenesulfonyl chloride (742 mg, 3.89 mmol) were added, and the mixture was stirred vigorously for two hours. The aqueous fraction was separated and extracted several times with chloroform. The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with 2-7% methanol in dichloromethane) followed by recrystallization from acetonitrile to provide 1-{[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanecarboxamide as a tan crystalline solid, mp 221-223° C.

Workup

  1. stirringthe mixture was stirred vigorously for two hours
  2. customThe aqueous fraction was separated
  3. extractionextracted several times with chloroform
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (eluting with 2-7% methanol in dichloromethane)
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-c9f62e42ed4348989c4d385f680cb9f6
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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