4-Toluenesulfonyl chloride → (11S)-11-methyl-3-[2-(methylsulfonyl)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 549195Notes

Reaction equation

HRID 549195 reaction equation
[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[C:12](=[CH:13][C:14]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:16]=4)[N:11]=[CH:10][C:9]=3[N:24]=[C:6]2[CH2:5][O:4][CH2:3]1.C1C=C(Cl)C=C(C(OO)=O)C=1.[NH4+:36].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O.C(Cl)Cl>[CH3:1][C@@H:2]1[N:7]2[C:8]3[C:17]4[C:12](=[CH:13][C:14]([CH2:18][CH2:19][S:20]([CH3:23])(=[O:21])=[O:22])=[CH:15][CH:16]=4)[N:11]=[C:10]([NH2:36])[C:9]=3[N:24]=[C:6]2[CH2:5][O:4][CH2:3]1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 67157340(11S)-11-methyl-3-[2-(methylsulfonyl)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 58406169(11S)-11-methyl-3-[2-(methylsulfonyl)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 200-mL, round-bottomed flask was charged with (11S)-11-methyl-3-[2-(methylsulfonyl)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (0.45 g, 1.31 mmol) and CH2Cl2 (75 mL). The mixture was stirred at ambient temperature and MCPBA (0.45 g, 50% purity) was then added slowly in portions. The reaction was stirred at ambient temperature for 2 hours. Concentrated aqueous NH4OH solution (25 mL) was then slowly added to the reaction mixture followed by careful addition of p-toluenesulfonyl chloride (0.27 g, 1.44 mmol). The reaction was stirred rapidly at ambient temperature overnight. The reaction was then treated with H2O (100 mL) and vigorous stirring was maintained for 2 hours. The layers were then separated and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were concentrated under reduced pressure. Chromatography (SiO2, 0-15% CMA/CHCl3) gave a white solid that was crystallized from acetonitrile to give 0.12 g of (11S)-11-methyl-3-[2-(methylsulfonyl)ethyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a white, crystalline solid, mp 205-206° C.

Workup

  1. stirringThe reaction was stirred at ambient temperature for 2 hours
  2. stirringThe reaction was stirred rapidly at ambient temperature overnight
  3. stirringvigorous stirring
  4. temperaturewas maintained for 2 hours
  5. customThe layers were then separated
  6. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  7. concentrationThe combined organic layers were concentrated under reduced pressure
  8. customChromatography (SiO2, 0-15% CMA/CHCl3) gave a white solid
  9. customthat was crystallized from acetonitrile

Sources & evidence

ORD record
ord-903a7d41e3624db096c824715c0b92b5
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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