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

HRID 419292Notes

Reaction equation

HRID 419292 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:21]4[CH2:22][CH2:23][O:24][CH2:25][C:20]4=[N:19][C:14]=3[CH:15]=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:21]4[CH2:22][CH2:23][O:24][CH2:25][C:20]4=[N:19][C:14]=3[C:15]([NH2:38])=[N:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 666501493-(benzyloxy)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinoline

Product 1

HCID 116099093-(benzyloxy)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1-liter round bottom flask was charged with 3-(benzyloxy)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (5.0 g, 15.1 millimoles (mmol)) and dichloromethane (200 mL). To this solution was slowly added in small portions 3-chloroperoxybenzoic acid (mCPBA) (5.2 g of 50% pure material, 15.1 mmol, 1.0 eq). The reaction was maintained at room temperature for 3 hours. Concentrated ammonium hydroxide (100 mL) was added followed by p-toluenesulfonyl chloride (3.2 g, 16.6 mmol, 1.1 eq) in small portions. The reaction was maintained at room temperature overnight. The reaction was quenched with water (200 mL) and stirred for an additional hour. The aqueous layer was separated and extracted with dichloromethane (3×50 mL). The combined organic fractions were concentrated to provide 3-(benzyloxy)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as an off-white solid. A small amount of product was recrystallized from acetonitrile and carried on to the next step.

Workup

  1. temperatureThe reaction was maintained at room temperature overnight
  2. customThe reaction was quenched with water (200 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with dichloromethane (3×50 mL)
  5. concentrationThe combined organic fractions were concentrated

Sources & evidence

ORD record
ord-0cdb21c816864ce2b22232ccebef1d28
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Reaction notes

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