Potassium cyanate → HCID 136136827, compound

HRID 1930052Notes

Reaction equation

HRID 1930052 reaction equation
Cl.[NH2:2][CH:3]([C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=O.[O-:26][C:27]#[N:28].[K+]>CN(C=O)C>[F:13][C:7]1[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=1[C:4]1[NH:28][C:27](=[O:26])[NH:2][C:3]=1[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH:23]([CH3:25])[CH3:24])=[N:21][N:22]=2)[N:19]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 68562544HCID 68562544, compound

Product 1

HCID 136136827HCID 136136827, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-amino-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone hydrochloride (1.18 g, 3.21 mmol) in DMF (10 mL) was added potassium cyanate (0.65 g, 8.0 mmol). The reaction mixture was stirred at about 110° C. for about 2 h. The temperature was reduced to about 80° C. and stirring continued for about 15 h. The solvent was removed under reduced pressure. The crude material was purified by RP-HPLC (Table 1, Method f). The appropriate fractions were combined and solvent removed under reduced pressure. The sample was dissolved in DCM (20 mL) and washed with saturated NaHCO3 solution (3×10 mL). The organic layer was dried over MgSO4, filtered, and solvent removed under reduced pressure to afford a solid that was dried under vacuum to give the title compound (0.09 g, 8%): LC/MS (Table 1, Method a) Rt=2.25 min; MS m/z: 357.1 (M+H)+.

Workup

  1. customwas reduced to about 80° C.
  2. stirringstirring
  3. waitcontinued for about 15 h
  4. customThe solvent was removed under reduced pressure
  5. customThe crude material was purified by RP-HPLC (Table 1, Method f)
  6. customsolvent removed under reduced pressure
  7. dissolutionThe sample was dissolved in DCM (20 mL)
  8. washwashed with saturated NaHCO3 solution (3×10 mL)
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. customsolvent removed under reduced pressure
  12. customto afford a solid
  13. customthat was dried under vacuum

Sources & evidence

ORD record
ord-76cca2134be64b48a5785b215db2531f
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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