Triethylamine → HCID 86612730, compound

HRID 2075475Notes

Reaction equation

HRID 2075475 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:25]=[CH:24][C:15]([C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[O:17])=[CH:14][CH:13]=2)=[N:2]1.[CH:26]([O:29][C:30]1[C:31](=O)[C:32](=[O:38])[C:33]=1[O:34]C(C)C)([CH3:28])[CH3:27].C(N(CC)CC)C>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:31]4[C:32](=[O:38])[C:33](=[O:34])[C:30]=4[O:29][CH:26]([CH3:28])[CH3:27])[CH2:20][CH2:19]3)=[O:17])=[CH:24][CH:25]=2)=[N:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1823143,4-Diisopropoxy-3-cyclobutene-1,2-dioneHCID 11427553(4-((1E)-2-(1H-Indazol-3-yl)ethenyl)phenyl)-1-piperazinylmethanone

Product 1

HCID 86612730HCID 86612730, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}piperazine (1.0 g, 2.5 mmol) obtained in Example 18 was dissolved in methanol (9.9 mL), and the solution was added with 3,4-diisopropoxy-3-cyclobutene-1,2-dione (0.69 g, 3.5 mmol) and triethylamine (0.69 mL, 4.9 mmol), followed by stirring at room temperature for 13 hours. The reaction mixture was concentrated under reduced pressure, and the crude product was added with ethanol, followed by stirring. The deposited crystal was collected by filtration to obtain (E)-3-{4-[4-(2-(1H-indazol-3-yl)vinyl)benzoyl]piperazin-1-yl}-4-isopropoxy-3-cyclobutene-1,2-dione (0.94 g, 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe crude product was added with ethanol
  3. stirringby stirring
  4. filtrationThe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-38a0ec39b22d41f1a1dbe0b18df17d0d
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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