Triethylamine → HCID 86678207, compound

HRID 1747562Notes

Reaction equation

HRID 1747562 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:19][CH:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:21]([F:24])([F:23])[F:22])[C:8]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:15])=[O:14])=[N:9]2)=[CH:4][CH:3]=1.C[Si]([C:35]#[CH:36])(C)C.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.[Cu](I)I.O>[C:35]([C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:19][CH:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[C:21]([F:24])([F:22])[F:23])[C:8]([NH:12][S:13]([CH2:16][CH2:17][CH3:18])(=[O:14])=[O:15])=[N:9]2)=[CH:4][CH:3]=1)#[CH:36]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 2724141Tetrabutylammonium FluorideHCID 71294052HCID 71294052, compound

Product 1

HCID 86678207HCID 86678207, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Compound 77 (70.0 mg, 0.127 mmol) obtained in Example 74 was dissolved in DMF (2.00 mL). To the solution were added trimethylsilylacetylene (0.089 mL, 0.634 mmol), triethylamine (0.088 mL, 0.634 mmol), copper iodide (I) (9.66 mg, 0.051 mmol), and tetrakis (triphenylphosphine)palladium (29.3 mg, 0.025 mmol), and the mixture was stirred at 120° C. for 30 minutes. Water was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/3). The obtained purified product was dissolved in THF (1.80 mL). Tetrabutylammonium fluoride (1.0 mol/L solution in THF, 0.107 mL, 0.107 mmol) was added and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 1/1) to give Compound 79 (25.7 mg, 46% yield).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washWashing with saturated brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/3)
  8. customThe obtained purified product
  9. dissolutionwas dissolved in THF (1.80 mL)
  10. stirringthe mixture was stirred at room temperature for 2 hours
  11. extractionExtraction with ethyl acetate
  12. washwashing with saturated brine
  13. dry with materialdrying over anhydrous magnesium sulfate
  14. filtrationAfter filtration
  15. customthe solvent in the filtrate was evaporated under reduced pressure
  16. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 1/1)

Sources & evidence

ORD record
ord-0ac5c74da0564c01ad06179996132236
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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