Water → HCID 86620797, compound

HRID 554460Notes

Reaction equation

HRID 554460 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]([NH:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:8]=1)=[O:4].B.[OH2:31]>O1CCCC1>[F:1][C:2]([F:29])([F:28])[C:3]([OH:31])=[O:4].[F:29][C:2]([F:1])([F:28])[CH2:3][NH:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:9]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:20])=[O:19])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 86620798HCID 86620798, compound

Product 1

HCID 86620797HCID 86620797, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (15 mL) of 2,2,2-trifluoro-N-({1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)acetamide (300 mg) in tetrahydrofuran was cooled at 0° C., 1 mol/L tetrahydrofuran solution of borane (2.84 mL) was added, and the mixture was stirred at room temperature for 5 hr and then at 50° C. for 3 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1), and the obtained oil was purified by preparative HPLC. The purified product was concentrated under reduced pressure, and the crystals precipitated during the process were collected by filtration. The crystals were recrystallized from ethyl acetate to give the title compound as colorless crystals (yield 70 mg, 20%).

Workup

  1. waitat 50° C. for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→2:1)
  7. customthe obtained oil was purified by preparative HPLC
  8. concentrationThe purified product was concentrated under reduced pressure
  9. customthe crystals precipitated during the process
  10. filtrationwere collected by filtration
  11. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2adfb916df524c0498f7e4ebc7c16e7a
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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