Water → 2-[(11R)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

HRID 549116Notes

Reaction equation

HRID 549116 reaction equation
[O-][N+:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[N:12]3[C@@H:18]([C:19]([OH:22])([CH3:21])[CH3:20])[CH2:17][O:16][CH2:15][C:13]3=[N:14][C:4]=2[CH:3]=1.[NH4+:23].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.O>C(Cl)Cl>[NH2:23][C:3]1[C:4]2[N:14]=[C:13]3[CH2:15][O:16][CH2:17][C@H:18]([C:19]([OH:22])([CH3:21])[CH3:20])[N:12]3[C:5]=2[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 671565972-[(11R)-5-oxido-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

Product 1

HCID 115656382-[(11R)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-[(11R)-5-Oxido-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol (798 mg, 2.67 mmol) was dissolved in 25 mL of CH2Cl2 and treated with 5 mL of concentrated NH4OH solution. The mixture was stirred rapidly and p-toluenesulfonyl chloride (534 mg, 2.80 mmol) was carefully added. Rapid stirring was continued for 2 hours. The reaction mixture was then treated with 25 mL of H2O and the layers were separated. The aqueous portion was extracted with additional CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10% methanol/CHCl3) gave a light yellow foam. Crystallization from ethyl acetate gave 2-[(11R)-6-amino-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-11-yl]propan-2-ol (220 mg) as white crystals, mp 216-217° C.

Workup

  1. stirringRapid stirring
  2. customthe layers were separated
  3. extractionThe aqueous portion was extracted with additional CH2Cl2 (3×20 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customChromatography (SiO2, 10% methanol/CHCl3) gave a light yellow foam
  8. customCrystallization from ethyl acetate

Sources & evidence

ORD record
ord-318afa6751a04478998d98d24037dd91
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

Loading…