Triethylsilane → HCID 178437073, compound

HRID 399946Notes

Reaction equation

HRID 399946 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:30])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:25][CH:24]([CH2:26][CH3:27])[O:23][CH:22](O)[CH2:21]3)[C:11]=2[Cl:29])[CH:5]=[N:4]1)[CH3:2].C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:30])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:21][CH2:22][O:23][CH:24]([CH2:26][CH3:27])[CH2:25]3)[C:11]=2[Cl:29])[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 178437075HCID 178437075, compound

Product 1

HCID 178437073HCID 178437073, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 500 mg (1.09 mmol) of 1-ethyl-4-(2-chloro-3-(6-ethyl-2-hydroxymorpholin-4-yl)-4-methylsulfonylbenzoyl)-5-hydroxypyrazole in 3 mL of trifluoroacetic acid was treated with 1 mL of triethylsilane at ambient temperature and stirred vigorously for 2 hours. The solvent was removed by evaporation under reduced pressure and the orange residue obtained was partitioned between dichloromethane and water. The organic solution was dried over sodium sulfate and concentrated by evaporation under reduced pressure. The solid residue was recrystallized from ethanol to obtain 210 mg (44 percent of theory) of the title compound as light orange-brown crystals.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe orange residue obtained
  3. customwas partitioned between dichloromethane and water
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e39f861ff883438eaf5a766c2c9c6d5c
Source dataset
uspto-grants-1998_10
Patent number
US05824802

Reaction notes

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