Sodium Thiosulfate → HCID 86696534, compound

HRID 1630302Notes

Reaction equation

HRID 1630302 reaction equation
[OH:1][C:2]1([C:8]#[C:9][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH2:19][C:20]#[CH:21])=[C:12]([NH2:22])[N:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:23]N1C(=O)CCC1=O.C([O-])(=O)C.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[Cl:23][C:15]1[N:16]([CH2:19][C:20]#[CH:21])[C:17]2[C:13]([N:14]=1)=[C:12]([NH2:22])[N:11]=[C:10]([C:9]#[C:8][C:2]1([OH:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[N:18]=2

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 517044Potassium AcetateHCID 86696535HCID 86696535, compound

Product 1

HCID 86696534HCID 86696534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The formula (9) compound: 2-[2-(1-hydroxycyclohexyl)-1-ethyn-1-yl]-N9-propargyladenine (200 mg, 0.67 mmol) was dissolved in dimethylformamide (7 mL), and N-chlorosuccinimide (180 mg, 1.3 mmol) and potassium acetate (20 mg, 0.20 mmol) was added thereto, and the mixture was stirred for 28.5 hours. A saturated sodium thiosulfate aqueous solution was added thereto to stop the reaction, and then the mixture was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was suspended in chloroform, and the solid was collected by filtration to give the product of interest (49 mg, 0.15 mmol, 22%).

Workup

  1. customthe reaction
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. filtrationthe solid was collected by filtration
  7. customto give the product of interest (49 mg, 0.15 mmol, 22%)

Sources & evidence

ORD record
ord-f5264bd3f67d4465b88a82917e20012e
Source dataset
uspto-grants-2014_07
Patent number
US08791126B2

Reaction notes

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