N-Iodosuccinimide → HCID 136102521, compound

HRID 1993155Notes

Reaction equation

HRID 1993155 reaction equation
[CH:1]1([C:7]2[N:15]3[C:10]([C:11](=[O:16])[NH:12][CH:13]=[N:14]3)=[CH:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I:17]N1C(=O)CCC1=O>CN(C=O)C.O>[CH:1]1([C:7]2[N:15]3[C:10]([C:11](=[O:16])[NH:12][CH:13]=[N:14]3)=[C:9]([I:17])[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 136102522HCID 136102522, compound

Product 1

HCID 136102521HCID 136102521, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 7-cyclohexylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (130 mg, 0.6 mmol) in DMF (0.6 mL) was added N-iodosuccinimide (700 mg, 0.003 mol) and the reaction mixture stirred at 55° C. for 20 h. After this time the mixture was diluted with water (50 mL) and extracted with EtOAc (4×40 mL). The organic extracts were washed with water (4×40 mL), treated with sodium thiosulfate and brine, dried over Na2SO4 and concentrated in vacuo to afford 7-cyclohexyl-5-iodoimidazo[5,1-f][1,2,4]triazin-4(3H)-one. 1H NMR (400 MHz—DMSO-d6) δ 1.34-1.37 (m, 3H), 1.52-1.56 (m, 2H), 1.76-1.88 (m, 5H), 3.06-3.08 (m, 1H) 7.87 (s, 1H) 11.78 (s, 1H); MS (ES+): m/z: 344.95 (100) [MH+]. HPLC: tr=2.95 min (OpenLynx: polar—5 min).

Workup

  1. extractionextracted with EtOAc (4×40 mL)
  2. washThe organic extracts were washed with water (4×40 mL)
  3. additiontreated with sodium thiosulfate and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3359ac9407084e15ad0a4179edbbd4f8
Source dataset
uspto-grants-2010_01
Patent number
US07651687B2

Reaction notes

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