Water → HCID 22339441, compound

HRID 1006217Notes

Reaction equation

HRID 1006217 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-3,5dione (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-eb73fdbb2b9c4083b6fe20627ca335d6
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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