Water → HCID 23653550, compound

HRID 602265Notes

Reaction equation

HRID 602265 reaction equation
[CH3:1][CH:2]1[C:7]2=[N:8][C:9]3[CH:10]=[N+:11]([O-])[C:12]4[C:17]([C:18]=3[N:6]2[C@@H:5]([CH3:20])[CH2:4][O:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=4.[OH-].[NH4+:22].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:1][CH:2]1[C:7]2=[N:8][C:9]3[C:10]([NH2:22])=[N:11][C:12]4[C:17]([C:18]=3[N:6]2[C@@H:5]([CH3:20])[CH2:4][O:3]1)=[CH:16][CH:15]=[CH:14][CH:13]=4

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67273561HCID 67273561, compound

Product 1

HCID 23653550HCID 23653550, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of (11S)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (85 mg, 0.316 mmol) in 5 mL of CH2Cl2 was treated with 1 mL of concentrated aqueous ammonium hydroxide and stirred vigorously. p-Toluenesulfonyl chloride (60 mg, 0.316 mmol) was added in one portion. The following day the reaction was treated with 5 mL of H2O and 10 mL of CH2Cl2, and the layers were separated. The organic layer was washed sequentially with saturated NaHCO3 solution (2×) and brine, dried over Na2SO4, filtered, and concentrated to give a light yellow solid. Chromatography (AFC, SiO2, 0-20% CMA/CHCl3) afforded (11s)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (25 mg) as a white solid, m.p. 218-223° C.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed sequentially with saturated NaHCO3 solution (2×) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light yellow solid

Sources & evidence

ORD record
ord-8703985a0122477197f7ec602f9a4807
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

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