Sodium Iodide → HCID 86709401, compound

HRID 2172266Notes

Reaction equation

HRID 2172266 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].FC(F)(F)C(O)=O.[CH3:16][C@H:17]1[CH2:22][NH:21][C@H:20]([CH3:23])[CH2:19][N:18]1[C:24]1[CH:43]=[CH:42][C:27]([O:28][CH2:29][C@@H:30]2[O:35][C:34]3=[N:36][C:37]([N+:39]([O-:41])=[O:40])=[CH:38][N:33]3[CH2:32][CH2:31]2)=[CH:26][CH:25]=1.Cl[CH2:45][C:46]1[CH:51]=[CH:50][C:49]([O:52][C:53]2[CH:58]=[CH:57][C:56]([O:59][C:60]([F:63])([F:62])[F:61])=[CH:55][CH:54]=2)=[CH:48][CH:47]=1.CC(C)([O-])C.[Na+]>O.CN1CCCC1=O>[CH3:16][C@H:17]1[CH2:22][N:21]([CH2:45][C:46]2[CH:47]=[CH:48][C:49]([O:52][C:53]3[CH:58]=[CH:57][C:56]([O:59][C:60]([F:61])([F:62])[F:63])=[CH:55][CH:54]=3)=[CH:50][CH:51]=2)[C@H:20]([CH3:23])[CH2:19][N:18]1[C:24]1[CH:25]=[CH:26][C:27]([O:28][CH2:29][C@@H:30]2[O:35][C:34]3=[N:36][C:37]([N+:39]([O-:41])=[O:40])=[CH:38][N:33]3[CH2:32][CH2:31]2)=[CH:42][CH:43]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 222930671-[4-(Chloromethyl)phenoxy]-4-(trifluoromethoxy)benzeneHCID 23676156Sodium t-butoxideHCID 86709402HCID 86709402, compound

Product 1

HCID 86709401HCID 86709401, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (135 mg) and sodium iodide (146 mg) were added to an N-methylpyrrolidone solution (6 ml) of (R)-7-[4-((2S,5R)-2,5-dimethyl-piperazin-1-yl)phenoxymethyl]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine trifluoroacetate (343 mg) and 1-(chloromethyl)-4-[4-(trifluoromethoxy)phenoxy]benzene (269 mg), and the mixture was stirred at 60° C. for 3 hours. Sodium tert-butoxide (112 mg) was added to the mixture and stirred at room temperature for 3 hours. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→ethyl acetate:n-hexane=3:1) to afford the title compound as a pale brown amorphous compound (200 mg).

Workup

  1. stirringstirred at room temperature for 3 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1→ethyl acetate:n-hexane=3:1)

Sources & evidence

ORD record
ord-d179a5e3a6e64c16a24e8f0af8d40122
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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