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Trifluoroacetic acid → 2-[4-(Benzoxazol-2-yl)piperazin-1-yl]-1-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazole-2,4'-piperidin]-1'-yl)ethanone

HRID 856378
Notes
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Reaction equation

HRID 856378 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:31]([CH:32]=1)[CH2:30][C:8]1([CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][N:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)[O:7]2)([O-:3])=[O:2].FC(F)(F)C(O)=O.C(N(CC)CC)C.Cl[C:48]1[O:49][C:50]2[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=2[N:52]=1>C(Cl)Cl.O>[O:49]1[C:50]2[CH:56]=[CH:55][CH:54]=[CH:53][C:51]=2[N:52]=[C:48]1[N:19]1[CH2:20][CH2:21][N:16]([CH2:15][C:14]([N:11]2[CH2:12][CH2:13][C:8]3([O:7][C:6]4=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:32][N:31]4[CH2:30]3)[CH2:9][CH2:10]2)=[O:29])[CH2:17][CH2:18]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 119862-ChlorobenzoxazoleHCID 69480722Tert-butyl 4-[2-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazol-2,4'-piperidin]-1'-yl)-2-oxoethyl]piperazine-1-carboxylate

Product 1

HCID 694815622-[4-(Benzoxazol-2-yl)piperazin-1-yl]-1-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazole-2,4'-piperidin]-1'-yl)ethanone
Yield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-[2-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazole-2,4′-piperidine]-1′-yl)-2-oxoethyl]piperazine-1-carboxylate prepared in Example 653 (227 mg, 0.50 mmol) was dissolved in methylene chloride (5 ml). To the solution, trifluoroacetic acid (5 ml) was added followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. To the residue, methylene chloride (1 ml) and triethylamine (1 ml) were added followed by stirring at room temperature for 5 minutes, and then the solution was concentrated under reduced pressure. The residue was dissolved in DMF (5 ml). To the solution, triethylamine (0.21 ml, 1.52 mmol) and 2-chlorobenzoxazole (86 μl, 0.76 mmol) were added followed by stirring at 80° C. for 2 hours. To the reaction mixture, water was added, and the mixture was extracted with methylene chloride. The organic phase was dried over magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The residue was crystallized from methylene chloride-ethyl acetate to afford 2-[4-(benzoxazol-2-yl)piperazin-1-yl]-1-(2,3-dihydro-6-nitrospiro[imidazo[2,1-b]oxazole-2,4′-piperidin]-1′-yl)ethanone (99 mg, 42%) as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue, methylene chloride (1 ml) and triethylamine (1 ml) were added
  3. stirringby stirring at room temperature for 5 minutes
  4. concentrationthe solution was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DMF (5 ml)
  6. stirringby stirring at 80° C. for 2 hours
  7. extractionthe mixture was extracted with methylene chloride
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe resulting filtrate was concentrated under reduced pressure
  11. customThe residue was crystallized from methylene chloride-ethyl acetate

Sources & evidence

ORD record
ord-df5646eb90414d24831303dbe12ad359
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07262212B2

Reaction notes

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