HCID 67156987, compound → HCID 135475882, compound

HRID 549118Notes

Reaction equation

HRID 549118 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]3[N:22]4[C@@H:23]([C:27]([F:30])([CH3:29])[CH3:28])[CH2:24][O:25][CH2:26][C:21]4=[N:20][C:14]=3[C:15]([NH2:19])=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:19][C:15]1[C:14]2[N:20]=[C:21]3[CH2:26][O:25][CH2:24][C@H:23]([C:27]([F:30])([CH3:29])[CH3:28])[N:22]3[C:13]=2[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=2)[N:16]=1

Participants

4

Reactant 1

HCID 67156987HCID 67156987, compound

Product 1

HCID 135475882HCID 135475882, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(11R)-3-(Benzyloxy)-11-(1-fluoro-1-methylethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (310 mg, 0.763 mmol) was dissolved in ethanol (50 mL) and the solution was placed in a pressure bottle. Palladium on carbon (10%, 140 mg) was added and the reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa) overnight. The reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with 1:1 CH2Cl2/ethanol and the combined filtrates were concentrated under reduced pressure to give an off white solid. Chromatography (SiO2, 30-50% CMA/CHCl3) followed by recrystallization from 1,2-dichloroethane gave (11R)-6-amino-11-(1-fluoro-1-methylethyl)-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-3-ol (63 mg) as a white powder, mp 219-221° C.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with 1:1 CH2Cl2/ethanol
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto give an off white solid
  6. customChromatography (SiO2, 30-50% CMA/CHCl3) followed by recrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-de261a16dfb445a9a90695ef399fbd99
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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