Trifluoroacetic acid → HCID 86714579, compound

HRID 2274468Notes

Reaction equation

HRID 2274468 reaction equation
[NH2:1][C:2]1[N:3]([CH2:27][CH3:28])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[N:13](COCC[Si](C)(C)C)[CH:14]=[CH:15][N:16]=1)=[CH:8][CH:7]=[C:6]([Cl:26])[N:5]=2.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[N:3]([CH2:27][CH3:28])[C:4]2[C:9]([C:10](=[O:25])[C:11]=1[C:12]1[NH:16][CH:15]=[CH:14][N:13]=1)=[CH:8][CH:7]=[C:6]([Cl:26])[N:5]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714575HCID 86714575, compound

Product 1

HCID 86714579HCID 86714579, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-7-chloro-1-ethyl-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-1H-[1,8]naphthyridin-4-one (1.0 g, 2.38 mmol) was dissolved in 30 mL of dichoromethane. 30 mL of trifluoroacetic acid were added and the reaction mixture was stirred at room temperature for 3 h, until analytical HPLC showed complete consumption of the starting material. Solvents were removed under reduced pressure, and ethyl acetate was added to the residue. The solution was washed with saturated aqueous sodium bicarbonate. The formed precipitate was collected by filtration, then put to dry out overnight at 40° C. under vacuum, yielding 574 mg of beige powder.

Workup

  1. customconsumption of the starting material
  2. customSolvents were removed under reduced pressure, and ethyl acetate
  3. additionwas added to the residue
  4. washThe solution was washed with saturated aqueous sodium bicarbonate
  5. filtrationThe formed precipitate was collected by filtration
  6. customto dry out overnight at 40° C. under vacuum

Sources & evidence

ORD record
ord-18a2c9ec4c67447b8aca8b890b932a43
Source dataset
uspto-grants-2015_09
Patent number
US09126972B2

Reaction notes

Loading…