Water → HCID 22339441, compound

HRID 585140Notes

Reaction equation

HRID 585140 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:26]2[C:31](=[O:32])[NH:30][C:29](=[O:33])[CH:28]=[N:27]2)[CH:5]=[C:6]([CH3:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)O)[CH:10]=1.CS(O)(=O)=O.C([SiH](CC)CC)C.O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:26]2[C:31](=[O:32])[NH:30][C:29](=[O:33])[CH:28]=[N:27]2)[CH:5]=[C:6]([CH3:25])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 12052TriethylsilaneHCID 22339372HCID 22339372, compound

Product 1

HCID 22339441HCID 22339441, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(3-chloro-4-{3-[(4-fluoro-phenyl)-hydroxy-methyl]-4-hydroxy-phenoxy}-5-methyl-phenyl)-2H-[1,2,4]triazine-3,5-dione (0.4 g) in dichloromethane (25 mL) were added methanesulfonic acid (0.7 mL) and triethylsilane (1.5 mL) portionwise over 1 h. After a total of 1.5 h, water was added, the layers separated and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate, dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (10-50% THF/hexanes) to afford the title compound of this EXAMPLE as a colorless foam, 56 mg. MS Calc.:453.9; Found:452.

Workup

  1. customthe layers separated
  2. extractionthe aqueous layer extracted with dichloromethane
  3. washThe combined organic layers were washed with saturated sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo and flash
  6. customchromatographed on silica gel (10-50% THF/hexanes)

Sources & evidence

ORD record
ord-e911db4c5a5b4e7999660835a39c3e65
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

Loading…