2-Pyridinamine, 5-iodo- → HCID 25204257, compound

HRID 910241Notes

Reaction equation

HRID 910241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[O:20][CH2:21][CH2:22][N:23]=2)=[CH:15][CH:14]=1)=O.C(=O)([O-])O.[Na+].ClCCl.CO>C(O)C>[I:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4[O:20][CH2:21][CH2:22][N:23]=4)=[CH:17][CH:18]=3)[N:1]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 885792-Pyridinamine, 5-iodo-HCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 86631890HCID 86631890, compound

Product 1

HCID 25204257HCID 25204257, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Subsequently, 2-amino-5-iodopyridine (88 mg) and 2-bromo-1-[4-(4,5-dihydro-1,3-oxazol-2-yl)phenyl]-1-ethanone mg) were dissolved in ethanol (7 mL), and sodium hydrogencarbonate (34 mg) was added to the solution, followed by refluxing for 13 hours. Dichloromethane-methanol solution was added to the reaction mixture, and the mixture was washed with water and saturated saline, followed by drying over sodium sulfate anhydrate. The solvent was evaporated, and the residue was subjected to silica gel chromatography. Fractions eluted by dichloromethane-methanol (100:5) were concentrated under reduced pressure, to thereby yield the title compound (89 mg).

Workup

  1. temperatureby refluxing for 13 hours
  2. washthe mixture was washed with water and saturated saline
  3. dry with materialby drying over sodium sulfate anhydrate
  4. customThe solvent was evaporated
  5. washFractions eluted by dichloromethane-methanol (100:5)
  6. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-1db993a45dcb43d3af445d161c86e1a3
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

Loading…