Ethyl Acetate → HCID 68431845, compound

HRID 2092086Notes

Reaction equation

HRID 2092086 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10](=S)[NH:11][CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30].[N:31]([Si](C)(C)C)=[N+:32]=[N-:33].C(OCC)(=O)C>ClCCl.[Fe](Cl)(Cl)Cl>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH2:9][C:10]2[N:11]([CH2:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[N:33]=[N:32][N:31]=2)[N:5]=[CH:4][C:3]=1[NH:20][C@@H:21]1[CH2:26][C@@H:25]2[CH2:27][C@@H:23]([C:24]2([CH3:29])[CH3:28])[C@H:22]1[CH3:30]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 78378AzidotrimethylsilaneHCID 86647510HCID 86647510, compound

Product 1

HCID 68431845HCID 68431845, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

2-{5-Bromo-6-oxo-4-[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino]pyridazin-1(6H)-yl}-N-(pyridin-4-ylmethyl)ethanethioamide (38 mg, 0.077 mmol) in dichloromethane (1 mL) was mixed with azidotrimethylsilane (41 μL, 0.308 mmol) and iron trichloride (30 mg, 0.185 mmol) at room temperature and stirred at room temperature for 17 hours. After completion of the reaction, ethyl acetate was added, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (chloroform/methanol=50/1) to give the desired product (9 mg, 24% yield).

Workup

  1. additionwas added
  2. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (chloroform/methanol=50/1)

Sources & evidence

ORD record
ord-1910c922523740e79af2585607410df7
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…