Chloroform → HCID 58406154, compound

HRID 549120Notes

Reaction equation

HRID 549120 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([NH2:19])[C:13]1[N:20]=[C:21]3[CH2:26][O:25][CH2:24][C@H:23]([CH:27]([CH3:29])[CH3:28])[N:22]3[C:12]2=1)C1C=CC=CC=1.C(Cl)(Cl)Cl>C(O)C.[Pd]>[NH2:19][C:14]1[C:13]2[N:20]=[C:21]3[CH2:26][O:25][CH2:24][C@H:23]([CH:27]([CH3:28])[CH3:29])[N:22]3[C:12]=2[C:11]2[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=2)[N:15]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 11531190HCID 11531190, compound

Product 1

HCID 58406154HCID 58406154, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(11S)-2-(Benzyloxy)-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (530 mg, 1.36 mmol) was dissolved in ethanol (50 mL) and the solution was placed in a pressure bottle. Palladium on carbon (10%, 220 mg) was added and the reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa) for 20 hours. The reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with 1:1 CH2Cl2/ethanol (200 mL) and the combined filtrates were concentrated under reduced pressure to give a white solid. Chromatography (SiO2, 30-50% CMA/CHCl3) gave (11S)-6-amino-11-isopropyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-2-ol (240 mg) as a white powder, mp 208-210° 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 (200 mL)
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customto give a white solid

Sources & evidence

ORD record
ord-5a255bcb91294f5ab5e8c77a0395e575
Source dataset
uspto-grants-2011_05
Patent number
US07943609B2

Reaction notes

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