Sodium Thiosulfate → HCID 66716934, compound

HRID 2409595Notes

Reaction equation

HRID 2409595 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[C:4]([NH2:17])=[N:5][CH:6]=[C:7]([C:9]2[S:13][C:12]3=[N:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH:8]=1.C1C(=O)N([I:27])C(=O)C1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[F:19][C:2]([F:1])([F:18])[C:3]1[C:4]([NH2:17])=[N:5][CH:6]=[C:7]([C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16]([I:27])[N:11]3[N:10]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 66716967HCID 66716967, compound

Product 1

HCID 66716934HCID 66716934, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(trifluoromethyl)-5-(imidazo[2,1-b][1,3,4]thiadiazol-2-yl)pyridin-2-amine (0.244 g, 0.855 mmol, 1 eq) was dissolved in DMF (5 mL), and NIS (0.212 g, 0.941 mmol, 1.1 eq) was added. The reaction mixture was stirred at RT under N2 for 18 h and then poured into an aqueous solution of sodium thiosulfate (10%) and extracted with AcOEt. The organic phase was separated, washed with ice-water and ammonium chloride, dried (Na2SO4), filtered and evaporated to dryness. The residue was treated with Et2O, filtered off and dried affording the desired product (0.240 g, 68%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.27 min, [M+H]+ m/z 411.9.

Workup

  1. extractionextracted with AcOEt
  2. customThe organic phase was separated
  3. washwashed with ice-water and ammonium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. additionThe residue was treated with Et2O
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-c9a4af13d0e34b59b0db1ac197c92807
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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