Dichloromethane → HCID 5278920, compound

HRID 1695971Notes

Reaction equation

HRID 1695971 reaction equation
[CH3:1][C@@:2]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([N:27]4[CH2:32][CH2:31][N:30]([C:33](OC(C)(C)C)=O)[CH2:29][CH2:28]4)=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[O:6][C:5]2=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]2[CH2:3]1.Cl[CH2:41][Cl:42]>FC(F)(F)C(O)=O>[Cl:42][C:41]1[CH:19]=[CH:20][C:15]([CH2:33][N:30]2[CH2:31][CH2:32][N:27]([C:24]3[CH:23]=[CH:22][C:21]([C:18]4[CH:17]=[CH:16][C:15]([O:14][CH2:13][C@:2]5([CH3:1])[O:6][C:5]6=[N:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][N:4]6[CH2:3]5)=[CH:20][CH:19]=4)=[CH:26][CH:25]=3)[CH2:28][CH2:29]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 67276101HCID 67276101, compound

Product 1

HCID 5278920HCID 5278920, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

850 mg of (R)-2-methyl-2-(4′-(4-tert-butoxycarbonylpiperazin-1-yl)biphenyl-4-yloxymethyl)-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole was dissolved in 10 ml of trifluoroacetic acid and 5 ml of dichloromethane, followed by stirring at room temperature overnight. Thereafter, the reaction solution was concentrated under a reduced pressure, and then, 6 ml of dichloromethane and 6 ml of triethylamine were added thereto. The mixture was stirred at room temperature for 5 minutes, and it was then concentrated under a reduced pressure. The residue was dissolved in 10 ml of DMF, and then, 444.2 mg of 4-chlorobenzaldehyde and 672 mg of triacetoxy sodium borohydride were added thereto while cooled by ice, followed by stirring at room temperature overnight. Thereafter, an aqueous sodium bicarbonate solution and ethyl acetate were added to the reaction solution, the mixture was stirred, and the insoluble precipitate was removed by filtration. The filtrate was washed with water and ethyl acetate, and was then dried to obtain 730 mg (yield: 51.8%) of light yellow powders, (R)-2-(4′-(4-(4-chlorobenzyl)piperazin-1-yl)biphenyl-4-yloxymethyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole.

Workup

  1. concentrationThereafter, the reaction solution was concentrated under a reduced pressure
  2. addition6 ml of dichloromethane and 6 ml of triethylamine were added
  3. stirringThe mixture was stirred at room temperature for 5 minutes
  4. concentrationit was then concentrated under a reduced pressure
  5. dissolutionThe residue was dissolved in 10 ml of DMF
  6. addition444.2 mg of 4-chlorobenzaldehyde and 672 mg of triacetoxy sodium borohydride were added
  7. temperaturewhile cooled by ice
  8. stirringby stirring at room temperature overnight
  9. additionThereafter, an aqueous sodium bicarbonate solution and ethyl acetate were added to the reaction solution
  10. stirringthe mixture was stirred
  11. customthe insoluble precipitate was removed by filtration
  12. washThe filtrate was washed with water and ethyl acetate
  13. customwas then dried

Sources & evidence

ORD record
ord-dc7b776eb240459c974cf589c3050e17
Source dataset
uspto-grants-2012_04
Patent number
US08163753B2

Reaction notes

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