Triethylamine → HCID 86675895, compound

HRID 710023Notes

Reaction equation

HRID 710023 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH2:30][CH2:29]2)=[C:17]([NH:19][C:20]([C:22]2[O:23][C:24](Br)=[CH:25][CH:26]=2)=[O:21])[CH:18]=1)=[O:12].C[Si]([C:45]#[CH:46])(C)C.C(N(CC)CC)C>C(#N)C.[Cu]I>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[CH:14]=[CH:15][C:16]([N:28]2[CH2:33][CH2:32][N:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])[CH2:30][CH2:29]2)=[C:17]([NH:19][C:20]([C:22]2[O:23][C:24]([C:45]#[CH:46])=[CH:25][CH:26]=2)=[O:21])[CH:18]=1)=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 71234026HCID 71234026, compound

Product 1

HCID 86675895HCID 86675895, compoundYield 14.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
80 °C

Procedure

In a 20 mL scintillation vial, 5-bromo-furan-2-carboxylic acid [5-[3-(2-oxo-pyrrolidin-1-yl)-propylcarbamoyl]-2-(4-o-tolyl-piperazin-1-yl)-phenyl]-amide (0.1 g, 0.231 mmol) was taken in acetonitrile (5.0 mL). Trimethylsilyl acetylene (0.045 g, 0.462 mmol), CuI (0.009 g, 0.046 mmol), triethylamine (0.116 g, 1.155 mmol) and PdCl2(Ph3P) (0.032 g, 0.046 mmol) were added to this, and the solution was evacuated for 5 min and nitrogen purged and stirred at 80° C. for 4 h. LC-MS indicated the completion of the reaction. It was diluted with acetonitrile and filtered through celite and concentrated. The crude was dissolved in THF and stirred with TBAF (2.0 mL of 2 M solution in THF) at room temperature for 16 h. The reaction was concentrated and dissolved in methanol and purified on preparative HPLC using methanol/water as eluent to give the desired product (0.018 g, 14% yield).

Workup

  1. customwas evacuated for 5 min
  2. customnitrogen purged
  3. customthe completion of the reaction
  4. filtrationfiltered through celite
  5. concentrationconcentrated
  6. dissolutionThe crude was dissolved in THF
  7. stirringstirred with TBAF (2.0 mL of 2 M solution in THF) at room temperature for 16 h
  8. concentrationThe reaction was concentrated
  9. dissolutiondissolved in methanol
  10. custompurified on preparative HPLC

Sources & evidence

ORD record
ord-bb0e22985d9a4e8baa3fabbb62464345
Source dataset
uspto-grants-2015_11
Patent number
US09181226B2

Reaction notes

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