m-Chloroperbenzoic acid → HCID 67350501, compound

HRID 1672854Notes

Reaction equation

HRID 1672854 reaction equation
[CH3:1][NH:2][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+].[CH3:49][NH2:50].C1COCC1>ClCCl.C(Cl)(Cl)Cl>[CH3:1][NH:2][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:50][CH3:49])[N:4]=1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66615946Methylamine tetrahydrofuranHCID 67349305HCID 67349305, compound

Product 1

HCID 67350501HCID 67350501, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-5-[3-(7-Methylamino-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 (17.6 mg, 0.0388 mmol) obtained in Step 9 was dissolved in dichloromethane (2.5 mL), and the mixture was stirred at room temperature for 30 minutes after adding 3-chloroperbenzoic acid (20.5 mg, 0.0582 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 methylamine/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 156) (8.0 mg, 47%).

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. concentrationThe mixture was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1a181188bf27497c962870cc325d4b89
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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