Trimethylsilyl iodide → HCID 58137791, compound

HRID 2189465Notes

Reaction equation

HRID 2189465 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[N:20]=[CH:21][CH:22]=[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)=[CH:11][CH:10]=1)=O)(C)(C)C.I[Si](C)(C)C>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[N:20]=[CH:21][CH:22]=[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 58137740HCID 58137740, compound

Product 1

HCID 58137791HCID 58137791, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(tert-butoxycarbonylamino)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (66E) (100 mg, 0.24 mmol) in CH2Cl2 (4 mL) was added iodotrimethylsilane (86 μL, 0.6 mmol) dropwise. After addition, the reaction mixture was stirred at room temperature for 10 min. Analysis by LC/MS indicated the starting material was consumed. The reaction mixture was partitioned between CH2Cl2 and water, then the separated CH2Cl2 layer was washed with water, saturated aqueous NaHCO3, saturated aqueous NaCl, dried (anhydrous Na2SO4), and concentrated. The obtained crude residue was purified using a silica gel cartridge (12 g) eluting with a gradient of EtOAc (50-100%) in hexanes to afford 60 mg (79%) of the title compound as a yellow solid. HPLC/MS (Method B): retention time=2.03 min, [M+H]+=312.3.

Workup

  1. additionAfter addition
  2. customwas consumed
  3. customThe reaction mixture was partitioned between CH2Cl2 and water
  4. washthe separated CH2Cl2 layer was washed with water, saturated aqueous NaHCO3, saturated aqueous NaCl
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customThe obtained crude residue
  8. customwas purified
  9. washeluting with a gradient of EtOAc (50-100%) in hexanes

Sources & evidence

ORD record
ord-42fd5a54d3b2416fa6c881c2d308261a
Source dataset
uspto-grants-2012_12
Patent number
US08324241B2

Reaction notes

Loading…