Water → HCID 178519570, compound

HRID 1725473Notes

Reaction equation

HRID 1725473 reaction equation
[Cl:1][C:2]1[C:3]([F:37])=[C:4]([CH:34]=[CH:35][CH:36]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[CH:24][N:23](COCC[Si](C)(C)C)[N:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6].O>FC(F)(F)C([O-])=O>[Cl:1][C:2]1[C:3]([F:37])=[C:4]([CH:34]=[CH:35][CH:36]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:25]=[CH:24][NH:23][N:22]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 962WaterHCID 57562645HCID 57562645, compound

Product 1

HCID 178519570HCID 178519570, compound

Reagents, catalysts & solvents 1

HCID 84468TrifluoroacetateSolvent

Procedure

18 mg of (6-((4-(3-Chloro-2-fluorobenzoyl)piperazin-1-yl)methyl)-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyridin-2-amine was dissolved in 900 μl of trifluoroacetate and 100 μl of water followed by stirring at room temperature for 5 hours. The reaction solution was concentrated in vacuo, diluted with ethyl acetate, and then washed with saturated sodium bicarbonate, water and brine. The resulting organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1) to give the title compound.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, water and brine
  4. dry with materialThe resulting organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform to chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-3b5b808f399346239ab6489837a17cb0
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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