Trifluoroacetic acid → [4-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]phenylmethanone

HRID 856320Notes

Reaction equation

HRID 856320 reaction equation
C([O:5][C:6]([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.FC(F)(F)C(O)=O.C(N(CC)CC)C.C(Cl)(=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(Cl)Cl>[CH3:26][C:15]1([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:5])[CH2:9][CH2:10]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 6422Trifluoroacetic acidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 230810802-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

Product 1

HCID 23081094[4-(2-Methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]phenylmethanoneYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(4-tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole prepared in Example 306 (142 mg, 0.39 mmol), trifluoroacetic acid (1 ml) and methylene chloride (1 ml) was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride (2 ml). To the mixture, triethylamine (2 ml, 14.35 mmol) was added. To the solution, benzoyl chloride (54 μl, 0.46 mmol) was added with cooling on ice-bath followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with methylene chloride, washed with a saturated sodium hydrogencarbonate solution, water and a saturated saline solution in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was treated with diethyl ether to afford [4-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazin-1-yl]phenylmethanone (72 mg, yield 50%) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (2 ml)
  3. temperaturewith cooling on ice-bath
  4. stirringby stirring at room temperature for 1 hour
  5. washwashed with a saturated sodium hydrogencarbonate solution, water
  6. dry with materiala saturated saline solution in this order, dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. additionthe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-465439070291468a835aa94f1d3968d0
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…