Trifluoroacetic acid → HCID 66558550, compound

HRID 2172250Notes

Reaction equation

HRID 2172250 reaction equation
[F:1][C:2]([F:7])([F:6])C(O)=O.C(O[C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH:29]3[O:34][C:33]4=[N:35][C:36]([N+:38]([O-:40])=[O:39])=[CH:37][N:32]4[CH2:31][CH2:30]3)=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>>[N+:38]([C:36]1[N:35]=[C:33]2[N:32]([CH:37]=1)[CH2:31][CH2:30][CH:29]([CH2:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([N:18]3[CH2:17][CH2:16][N:15]([CH2:13][C:21]4[CH:26]=[CH:25][C:24]([O:27][C:2]([F:1])([F:6])[F:7])=[CH:23][CH:22]=4)[CH2:20][CH2:19]3)=[CH:26][CH:25]=1)[O:34]2)([O-:40])=[O:39]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70874212HCID 70874212, compound

Product 1

HCID 66558550HCID 66558550, compound

Procedure

Trifluoroacetic acid (6.0 ml) was added to 4-[4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperazine-1-carboxylic acid tert-butyl ester (200 mg), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and methylene chloride (2.0 ml) and triethylamine (2.0 ml) were added to the residue, followed by stirring at room temperature for 5 minutes. The reaction mixture was reconcentrated under reduced pressure. 1,2-Dichloroethane (5 ml), 4-(trifluoromethoxy)benzaldehyde (124 μl) and sodium triacetoxyborohydride (185 mg) were added to the residue, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1) and recrystallized from methylene chloride-isopropyl ether to afford the title compound as a white powder (211 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and methylene chloride (2.0 ml) and triethylamine (2.0 ml)
  2. additionwere added to the residue
  3. stirringby stirring at room temperature for 5 minutes
  4. addition1,2-Dichloroethane (5 ml), 4-(trifluoromethoxy)benzaldehyde (124 μl) and sodium triacetoxyborohydride (185 mg) were added to the residue
  5. stirringthe mixture was stirred at room temperature overnight
  6. additionWater was added to the reaction mixture
  7. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  8. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  9. dry with materialdried over sodium sulfate
  10. filtrationAfter filtering
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=10:0→methylene chloride:methanol=9:1)
  13. customrecrystallized from methylene chloride-isopropyl ether

Sources & evidence

ORD record
ord-102e15c3b18d4997b248a6dc83e49627
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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