Triethylamine → HCID 86612730, compound

HRID 2378756Notes

Reaction equation

HRID 2378756 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-668aa67919b64bf2b6f365a4c63995e2
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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