Hydrogen Peroxide → HCID 58223423, compound

HRID 41256Notes

Reaction equation

HRID 41256 reaction equation
C([C:3]1[C:4]([CH3:18])=[N:5][N:6]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([S:16][CH3:17])[S:8][C:7]=12)=O.[Mn]([O-])(=O)(=O)=O.[K+].[OH:25]O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:46]([CH2:49]C)CC)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>C1(C)C=CC=CC=1.CC(C)=O>[C:51]([O:55][C:49]([NH:46][C:3]1[C:4]([CH3:18])=[N:5][N:6]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([S:16][CH3:17])[S:8][C:7]=12)=[O:25])([CH3:54])([CH3:53])[CH3:52]

Participants

9

Reactant 6

HCID 784Hydrogen PeroxideHCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 516875Potassium PermanganateHCID 3507588Ethyl 7-formyl-6-methyl-2-(methylthio)pyrazolo[5,1-b]thiazole-3-carboxylate

Product 1

HCID 58223423HCID 58223423, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

To an acetone (7 mL) solution of ethyl 7-formyl-6-methyl-2-(methylthio)pyrazolo[5,1-b][1,3]thiazole-3-carboxylate (100 mg, 0.35 mmol), was added aqueous (3 mL) solution of potassium permanganate (83.4 mg, 0.53 mmol), and the mixture was stirred at room temperature for 45 minutes. To the reaction mixture, aqueous hydrogen peroxide was added, and insoluble matters were filtered off and then the organic solvent in the filtrate was distilled off under reduced pressure. The residue was subjected to cotton filtration, and a 2N aqueous solution of hydrochloric acid was added thereto to yield a solid, the obtained solid was filtered and dried. To a toluene (2 mL) solution of the obtained white solid (80.3 mg, 0.27 mmol) were added diphenylphosphoryl azide (63.1 μL, 0.29 mmol), triethylamine (44.7 μL, 0.32 mmol) and tert-butyl alcohol (122 μL, 1.33 mmol), and the mixture was stirred at 110° C. for two hours. The solvent in the reaction mixture was distilled off under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate: 25% then 66%) to obtain 35.7 mg (0.096 mmol) of the title compound.

Workup

  1. filtrationinsoluble matters were filtered off
  2. distillationthe organic solvent in the filtrate was distilled off under reduced pressure
  3. filtrationThe residue was subjected to cotton filtration
  4. additiona 2N aqueous solution of hydrochloric acid was added
  5. customto yield a solid
  6. filtrationthe obtained solid was filtered
  7. customdried
  8. stirringthe mixture was stirred at 110° C. for two hours
  9. distillationThe solvent in the reaction mixture was distilled off under reduced pressure
  10. customthe residue was purified by medium pressure silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-4ab51766ca7d43a5800ab829a3382bc8
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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