Hydrogen Peroxide → HCID 22479732, compound

HRID 2183279Notes

Reaction equation

HRID 2183279 reaction equation
O1CCCCC1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=2)[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:26]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[O:27])[CH:20]=2)=[N:8]1.OO.[OH-].[Na+].O>C(O)C>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([C:26]([NH:25][C:21]2[CH:20]=[C:19]([C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[C:12]([C:16]([NH2:18])=[O:17])[CH:11]=4)[NH:7][N:8]=3)[CH:24]=[CH:23][CH:22]=2)=[O:27])[CH:29]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 224802181-perhydro-2H-pyran-2-yl-3-[3-(3-pyridylcarbonylamino)phenyl]-1H-indazole-5-carboxamide

Product 1

HCID 22479732HCID 22479732, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Precursor, 1-perhydro-2H-pyran-2-yl-3-[3-(3-pyridylcarbonylamino) phenyl]-1H-indazole-5-carboxamide, was dissolved in ethanol (4 mL) . Hydrogen peroxide (4 mL, 30% wt) was added to the solution followed by 0.200 mL of 6.0 N NaOH aqueous solution. The suspension turned white upon heating to 60° C. for 3.5 h. The reaction could not be driven to completion even after addition of excess reagent. The reaction mixture was neutralized. A white precipitate formed upon addition of water. The solid was collected by filtration and dried in a vacuum oven at 40° C. overnight. A suspension of this solid in 10 mL of toluene was cooled to 0° C. HCl gas was bubbled through the suspension for 10 min before stirring the flask content at room temperature for 2 hours. The desired product was purified using preparatory HPLC (0.049 g, 30% yield over 3 steps): 1H NMR (CD3OD) 9.2 (d, 1H), 8.77 (dd, 1H), 8.7 (s, 1H), 8.4 (s, 1H), 8.39 (dt, 1H), 7.9-7.8 (m, 3H), 7.6-7.5 (m, 4H); ES-MS (m/z) 358 [M+H]+.

Workup

  1. customThe reaction could not
  2. additioneven after addition of excess reagent
  3. filtrationThe solid was collected by filtration
  4. customdried in a vacuum oven at 40° C. overnight
  5. additionA suspension of this solid in 10 mL of toluene
  6. temperaturewas cooled to 0° C
  7. customHCl gas was bubbled through the suspension for 10 min
  8. customThe desired product was purified

Sources & evidence

ORD record
ord-f0e97aab6f114fb495cd3bfe4ac01ba4
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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