m-Chloroperbenzoic acid → HCID 67351914, compound

HRID 1672857Notes

Reaction equation

HRID 1672857 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1[C:16]2[C:15](=[O:17])[N:14]([C:18]3[CH:19]=[C:20]([C:24]4[O:28][C:27](=[O:29])[N:26]([CH3:30])[N:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:6]=[C:5](SC)[N:4]=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)(O)[O-].[Na+].[CH2:50]([NH2:52])[CH3:51].C1COCC1>ClCCl.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:33])[C:3]1[C:16]2[C:15](=[O:17])[N:14]([C:18]3[CH:19]=[C:20]([C:24]4[O:28][C:27](=[O:29])[N:26]([CH3:30])[N:25]=4)[CH:21]=[CH:22][CH:23]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:6]=[C:5]([NH:52][CH2:50][CH3:51])[N:4]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66726184Ethylamine tetrahydrofuran2×HCID 67350101HCID 67350101, compound

Product 1

HCID 67351914HCID 67351914, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-5-[3-(7-Dimethylamino-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-3-methyl-1,3,4-oxadiazol-2(3H)-one (26.8 mg, 0.0573 mmol) obtained in Step 1 was dissolved in dichloromethane (5.0 mL), and the mixture was stirred at room temperature for 20 minutes after adding 3-chloroperbenzoic acid (22.8 mg, 0.0860 mmol). A saturated aqueous sodium bicarbonate solution and chloroform were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in THF (2.0 mL), and the mixture was stirred at 90° C. for 30 minutes under microwave (CEM; Discover; 250 watts) irradiation after adding a 2.0 mol/L ethylamine/THF solution (1.0 mL, 2.00 mmol). The mixture was further stirred at 90° C. for 135 minutes under microwave (CEM; Discover; 250 watts) irradiation after adding a 2.0 mol/L ethylamine/THF solution (1.0 mL, 2.00 mmol). The mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (Compound 159) (18.9 mg, 71%).

Workup

  1. customto separate the organic layer
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in THF (2.0 mL)
  5. stirringthe mixture was stirred at 90° C. for 30 minutes under microwave (CEM; Discover; 250 watts) irradiation
  6. stirringThe mixture was further stirred at 90° C. for 135 minutes under microwave (CEM; Discover; 250 watts) irradiation
  7. concentrationThe mixture was concentrated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac78a8eecc0e49ed9fe32583273807a3
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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