Chloroform → 3-[(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-3-yl]-N,N-dimethylpropanamide

HRID 1035583Notes

Reaction equation

HRID 1035583 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH3:19])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][C:6](/[CH:20]=[CH:21]/[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:7][CH:8]=2)[N:3]=1.C(Cl)(Cl)Cl>[Pd].C(O)C>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]3[CH2:18][O:17][CH2:16][C@H:15]([CH3:19])[N:14]3[C:10]=2[C:9]2[C:4](=[CH:5][C:6]([CH2:20][CH2:21][C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 67156540(2E)-3-[(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-3-yl]-N,N-dimethylprop-2-enamide

Product 1

HCID 584061433-[(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4',3':1,2]imidazo[4,5-c]quinolin-3-yl]-N,N-dimethylpropanamideYield 56.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent2×

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 (2E)-3-[(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-3-yl]-N,N-dimethylprop-2-enamide (210 mg, 0.60 mmol) dissolved in 50 mL of 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 24 hours. The reaction mixture was then filtered through a pad of CELITE filter agent. The pad was 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 120 mg of 3-[(11S)-6-amino-11-methyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinolin-3-yl]-N,N-dimethylpropanamide as white crystals, mp 235-237° C.

Workup

  1. additionwas then added
  2. stirringshaken under H2 at 50 PSI (3.4×105 Pa) for 24 hours
  3. filtrationThe reaction mixture was then filtered through a pad of CELITE
  4. filtrationfilter agent
  5. washThe pad was 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-015bf914662948c38310c0152e1a3fa4
Source dataset
uspto-grants-2013_10
Patent number
US08546383B2

Reaction notes

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