Sodium Thiosulfate → HCID 22063528, compound

HRID 1828464Notes

Reaction equation

HRID 1828464 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:5][CH:4]1[C:6]1[C:11](=[O:12])[N:10]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][C:19]3[S:20][CH:21]=[C:22]([CH:24]([CH3:26])[CH3:25])[N:23]=3)=[CH:16][C:9]2=[N:8][C:7]=1[N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.CC(C)=[O:35].OS(O)(=O)=O.O=[Cr](=O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O>[CH:24]([C:22]1[N:23]=[C:19]([CH2:18][CH2:17][C:15]2[CH:14]=[CH:13][N:10]3[C:11](=[O:12])[C:6]([CH:4]4[CH2:5][CH:3]4[C:2]([OH:35])=[O:1])=[C:7]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[N:8]=[C:9]3[CH:16]=2)[S:20][CH:21]=1)([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 22063735HCID 22063735, compoundHCID 131709961Jones' reagent2×

Product 1

HCID 22063528HCID 22063528, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[2-(Hydroxymethyl)cyclopropyl]-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4H-pyrido[1,2-a]pyrimidin-4-one (55 mg, 0.121 mmol) dissolved in acetone (10 ml) was added dropwise with Jones' reagent (130 μl, 0.363 mmol) under ice cooling with and stirred for 2 hours. Then, the reaction solution was further added with Jones' reagent (165 μl) and stirred for 2 hours. Then, the reaction was stopped with saturated sodium thiosulfate, and the reaction solution was extracted with chloroform. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=10:1) to obtain 2.2 mg (4%) of the title compound as yellow crystals.

Workup

  1. stirringstirred for 2 hours
  2. extractionthe reaction solution was extracted with chloroform
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by thin layer silica gel chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-20a0cc9e0faa400983fe2757a788a920
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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