Iodine → HCID 18447428, compound

HRID 1269898Notes

Reaction equation

HRID 1269898 reaction equation
II.C[Si](C)(C)[Si](C)(C)C.[NH:11]1[C:19]2[C:14](=[CH:15][C:16]([NH:20][CH2:21][CH:22]3[CH2:28][CH:27]4[N:29](NC(OCC)=O)[CH:24]([CH2:25][CH2:26]4)[CH2:23]3)=[CH:17][CH:18]=2)[CH:13]=[N:12]1>ClC(Cl)C>[CH:27]12[NH:29][CH:24]([CH2:25][CH2:26]1)[CH2:23][CH:22]([CH2:21][NH:20][C:16]1[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=1)[NH:11][N:12]=[CH:13]3)[CH2:28]2

Participants

5

Reactant 3

HCID 807IodineHCID 74057HexamethyldisilaneHCID 18447314HCID 18447314, compound

Product 1

HCID 18447428HCID 18447428, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

Iodine (599 mg, 2.36 mmol) was added to hexamethyldisilane (864 mg, 5.90 mmol) and the resulting mixture was heated to 70° C. with stirring. When the reaction solution became substantially colorless after violent reaction, it was cooled to room temperature. A solution of the ethyl 3-[(1H-indazol-5-ylamino)methyl]-8-azabicyclo[3.2.1]octane-8-carbamate (386 mg, 1.18 mmol) obtained in Example 541 in dichloroethane (8 ml) was added thereto, and the resulting mixture was stirred at 50° C. for 5 hours. The reaction was terminated by adding methanol (4 ml) under ice-cooling, and then the solvent was distilled off under reduced pressure. Chloroform/aqueous ammonia was added to the residue, followed by extraction with chloroform, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby N-(8-azabicyclo[3.2.1]oct-3-ylmethyl)-1H-indazol-5-amine (258 mg, 85%) was obtained.

Workup

  1. customafter violent reaction, it
  2. temperaturewas cooled to room temperature
  3. stirringthe resulting mixture was stirred at 50° C. for 5 hours
  4. customThe reaction was terminated
  5. additionby adding methanol (4 ml) under ice-
  6. temperaturecooling
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionChloroform/aqueous ammonia was added to the residue
  9. extractionfollowed by extraction with chloroform
  10. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  11. dry with materialdried over sodium sulfate
  12. distillationdistilled under reduced pressure
  13. customto remove the solvent

Sources & evidence

ORD record
ord-d7399a2494a14af4b39c7756355b7583
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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