Thiophenol → HCID 178520906, compound

HRID 1530002Notes

Reaction equation

HRID 1530002 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])[CH:24]=3)[S:10][C:11]=2[C:12]2[N:16]=[CH:15][N:14](C3CCCCO3)[N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:41]1([SH:47])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O1CCCC1.C(OCC)(=O)C>[C:41]1([S:47][CH2:32][CH2:31][C:30]([NH:29][C:25]2[CH:24]=[C:23]([C:9]3[S:10][C:11]([C:12]4[NH:16][CH:15]=[N:14][N:13]=4)=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=3)[CH:28]=[CH:27][N:26]=2)=[O:33])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 66854672HCID 66854672, compound

Product 1

HCID 178520906HCID 178520906, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-{4-phenyl-5-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-1,3-thiazol-2-yl}pyridin-2-yl)prop-2-enamide (92 mg, 0.2 mmol) prepared in Example 4-B (iii) in tetrahydrofuran (2.0 mL) were added triethylamine (30 mg, 0.3 mmol) and thiophenol (29 mg, 0.26 mmol), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate (25 mL), and washed with saturated aqueous sodium bicarbonate solution (25 mL). The aqueous layer was extracted with ethyl acetate (25 mL), and the combined organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in trifluoroacetic acid (8.0 mL), and the mixture was stirred at room temperature for 6 hr. Trifluoroacetic acid was evaporated under reduced pressure, and the residue was diluted with ethyl acetate (40 mL) and washed with saturated aqueous sodium bicarbonate solution (30 mL). The aqueous layer was separated and extracted with ethyl acetate (40 mL), and the combined organic layer was dried over anhydrous magnesium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (69 mg, 71%) as a white solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution (25 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (25 mL)
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (8.0 mL)
  7. stirringthe mixture was stirred at room temperature for 6 hr
  8. customTrifluoroacetic acid was evaporated under reduced pressure
  9. additionthe residue was diluted with ethyl acetate (40 mL)
  10. washwashed with saturated aqueous sodium bicarbonate solution (30 mL)
  11. customThe aqueous layer was separated
  12. extractionextracted with ethyl acetate (40 mL)
  13. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  14. filtrationThe insoluble material was filtered off
  15. concentrationthe filtrate was concentrated under reduced pressure
  16. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record
ord-0953edbf7a764f44874dc0d365b20972
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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