Water → HCID 178519567, compound

HRID 1725477Notes

Reaction equation

HRID 1725477 reaction equation
[F:1][C:2]1[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:24]=[CH:23][N:22](COCC[Si](C)(C)C)[N:21]=3)[CH:16]=[N:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5].O>FC(F)(F)C(O)=O>[F:1][C:2]1[C:36]([C:37]([F:39])([F:38])[F:40])=[CH:35][CH:34]=[CH:33][C:3]=1[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:24]=[CH:23][NH:22][N:21]=3)[CH:16]=[N:15][CH:14]=2)[CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 962WaterHCID 57562628HCID 57562628, compound

Product 1

HCID 178519567HCID 178519567, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.49 g of 6-((4-(2-fluoro-3-(trifluoromethyl)benzoyl)piperazin-1-yl)methyl)-N-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-3-yl)pyrazin-2-amine was dissolved in 25 ml of trifluoroacetic acid and 2.5 ml of water followed by stirring at room temperature for 2 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=5/1) to give the title compound as a solid. The resulting solid was dissolved in ethanol by heating to 80° C. The solution was charged with heptane, and heating was stopped. Then the solution was cooled slowly to room temperature. After heptane was further added, the precipitate was filtered and dried to give a crystal of 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=5/1)

Sources & evidence

ORD record
ord-d09ba5cfaffb43aab91c90b8ae0182f1
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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