Ethanol → (11S)-11-Methyl-3-(3-morpholin-4-yl-3-oxopropyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

HRID 1035581Notes

Reaction equation

HRID 1035581 reaction equation
C(O)C.[CH3:4][C@@H:5]1[N:10]2[C:11]3[C:20]4[C:15](=[CH:16][C:17](/[CH:21]=[CH:22]/[C:23]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[O:24])=[CH:18][CH:19]=4)[N:14]=[C:13]([NH2:31])[C:12]=3[N:32]=[C:9]2[CH2:8][O:7][CH2:6]1.C(Cl)(Cl)Cl>[Pd].CO.C(O)C>[CH3:4][C@@H:5]1[N:10]2[C:11]3[C:20]4[C:15](=[CH:16][C:17]([CH2:21][CH2:22][C:23]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)=[O:24])=[CH:18][CH:19]=4)[N:14]=[C:13]([NH2:31])[C:12]=3[N:32]=[C:9]2[CH2:8][O:7][CH2:6]1

Participants

6

Reactant 3

HCID 702EthanolHCID 6212ChloroformHCID 58406173(11S)-11-Methyl-3-[(1E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amine

Product 1

HCID 58406184(11S)-11-Methyl-3-(3-morpholin-4-yl-3-oxopropyl)-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-6-amineYield 44.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

A 250-mL, glass Parr bottle was charged with palladium on carbon (10%, 0.05 g) and 2 mL of ethanol. A solution of (11S)-11-methyl-3-[(1E)-3-morpholin-4-yl-3-oxoprop-1-enyl]-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-6-amine (0.25 g, 0.63 mmol) dissolved in 125 mL of a 1:1 mixture of methanol/ethanol was then added. The reaction mixture was placed on Parr apparatus and shaken under H2 at 50 PSI (3.4×105 Pa) overnight at ambient temperature. The reaction mixture was treated with additional palladium on carbon (10%, 0.05 g) and shaken under H2 at 50 PSI (3.4×105 Pa) for 3 days. The reaction mixture was then filtered through a pad of CELITE filter agent. The pad rinsed with methanol and the combined filtrates were concentrated under reduced pressure to give a white solid. Chromatography (SiO2, 0-15% CMA/CHCl3) gave a white solid that was crystallized from acetonitrile to give 111 mg of the title compound as white crystals, mp 245-247° C.

Workup

  1. additionwas then added
  2. stirringshaken under H2 at 50 PSI (3.4×105 Pa) for 3 days
  3. filtrationThe reaction mixture was then filtered through a pad of CELITE
  4. filtrationfilter agent
  5. washThe pad rinsed with methanol
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. customto give a white solid
  8. customthat was crystallized from acetonitrile

Sources & evidence

ORD record
ord-bd039b69cb974a6fb7c794281909fc72
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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