Water → HCID 23081653, compound

HRID 856291Notes

Reaction equation

HRID 856291 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2([CH3:26])[O:19][C:18]3=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]3[CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl[C:28]1[O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.C(N(CC)CC)C.O>FC(F)(F)C(O)=O>[CH3:26][C:15]1([CH2:14][N:11]2[CH2:10][CH2:9][N:8]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[N:32]=3)[CH2:13][CH2:12]2)[O:19][C:18]2=[N:20][C:21]([N+:23]([O-:25])=[O:24])=[CH:22][N:17]2[CH2:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 230810802-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 23081653HCID 23081653, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-(4-tert-Butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 306 (500 mg, 1.36 mmol) was dissolved in trifluoroacetic acid (10 ml) followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and added methylene chloride (1 ml) and triethylamine (1 ml). The solution was stirred at room temperature for 5 minutes, and then concentrated under reduced pressure. The residue was dissolved in methylene chloride. To the solution, 2-chlorobenzoxazole (0.19 ml, 1.63 mmol) and triethylamine (0.23 ml, 1.63 mmol) were added followed by stirring at room temperature for 1 hour. The reaction mixture was poured into water, and extracted with methylene chloride. The organic phase was washed with a saturated saline solution, dried over magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1) and crystallized from methylene chloride-diisopropyl ether to afford 2-[4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]benzoxazole (325 mg, yield 62%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionadded methylene chloride (1 ml) and triethylamine (1 ml)
  3. stirringThe solution was stirred at room temperature for 5 minutes
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. stirringby stirring at room temperature for 1 hour
  7. extractionextracted with methylene chloride
  8. washThe organic phase was washed with a saturated saline solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (methylene chloride/methanol=100/1)
  13. customcrystallized from methylene chloride-diisopropyl ether

Sources & evidence

ORD record
ord-cad6f21fc4994b6388ddbf219424d35f
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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