Hydrochloric Acid → (R)-2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

HRID 920491Notes

Reaction equation

HRID 920491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8]C)[C:3]=1[C:10]1[NH:28][C:13]2=[CH:14][C:15]3[C:16](=[O:27])[N:17]([CH2:22][C@@H:23]([OH:26])[CH2:24][OH:25])[C:18](=[O:21])[C:19]=3[CH:20]=[C:12]2[N:11]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:10]1[NH:11][C:12]2=[CH:20][C:19]3[C:18](=[O:21])[N:17]([CH2:22][C@@H:23]([OH:26])[CH2:24][OH:25])[C:16](=[O:27])[C:15]=3[CH:14]=[C:13]2[N:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66687275(R)-2-(4-Chloro-2-methoxypyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Product 1

HCID 136340652(R)-2-(4-chloro-2-oxo-1,2-dihydropyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (R)-2-(4-chloro-2-methoxypyridin-3-yl)-6-(2,3-dihydroxypropyl)imidazo[4,5-f]isoindole-5,7(1H,6H)-dione (380 mg, 0.95 mmol) in 50 mL of dioxane was added 1 mL of conc. HCl. The mixture was heated to reflux and maintained for 3 h. The solvent was removed by rotary evaporation and the solid residue was triturated with n-butanol three times to give a white solid which was used directly in the next step. APCI MS: m/z 389.0 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturemaintained for 3 h
  4. customThe solvent was removed by rotary evaporation
  5. customthe solid residue was triturated with n-butanol three times
  6. customto give a white solid which

Sources & evidence

ORD record
ord-38a9e8be9456410799fc7a3623117ddc
Source dataset
uspto-grants-2016_03
Patent number
US09273055B2

Reaction notes

Loading…