Water → HCID 178519570, compound

HRID 1172416Notes

Reaction equation

HRID 1172416 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-ab9c2e843e5c46769a805ef3f82fd768
Source dataset
uspto-grants-2010_11
Patent number
US07834018B2

Reaction notes

Loading…