4-Toluenesulfonyl chloride → HCID 73152964, compound

HRID 2426351Notes

Reaction equation

HRID 2426351 reaction equation
C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:12][O:13][N:14]=[CH:15][C:16]1[N:17]([CH2:29][CH:30]([CH3:32])[CH3:31])[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.[OH-].[NH4+:34].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl.ClCCl>[CH3:12][O:13][N:14]=[CH:15][C:16]1[N:17]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[C:20]([NH2:34])[C:19]=2[N:28]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 76609476HCID 76609476, compound

Product 1

HCID 73152964HCID 73152964, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

mCPBA (1.75 g of 77% pure material, 7.79 mmol) was added in portions over a period of five minutes to a solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde O-methyloxime (1.1 g, 3.9 mmol) in chloroform (40 mL), and the reaction was stirred at room temperature for one hour. Ammonium hydroxide (20 mL) was added, and the resulting mixture was stirred for five minutes before the addition of p-toluenesulfonyl chloride (0.891 g, 4.68 mmol) in portions. The reaction mixture was stirred at room temperature for 1.5 hours. The aqueous layer was then separated and extracted with dichloromethane (3×30 mL). The combined organic fractions were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.2 g of crude product as a brown foamy solid. The crude product was dissolved in dichloromethane (15 mL) and purified by chromatography using a HORIZON HPFC system (FLASH 40M silica cartridge available from Biotage, Inc., eluting with 2% to 7% methanol in ethyl acetate). The resulting product (580 mg) was recrystallized from acetonitrile (10 mL), and the crystals were isolated by filtration, washed with diethyl ether, and dried overnight in a vacuum oven at 65° C. to provide 236 mg of 4-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-carbaldehyde O-methyloxime as a brown solid, mp 181-183° C.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1.5 hours
  2. customThe aqueous layer was then separated
  3. extractionextracted with dichloromethane (3×30 mL)
  4. dry with materialThe combined organic fractions were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide 2.2 g of crude product as a brown foamy solid
  8. custompurified by chromatography
  9. washa HORIZON HPFC system (FLASH 40M silica cartridge available from Biotage, Inc., eluting with 2% to 7% methanol in ethyl acetate)
  10. customThe resulting product (580 mg) was recrystallized from acetonitrile (10 mL)
  11. customthe crystals were isolated by filtration
  12. washwashed with diethyl ether
  13. customdried overnight in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-9554b5d1caf847ad8399f1cc6f003cd0
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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