Trifluoroacetic acid → HCID 178487158, compound

HRID 1750013Notes

Reaction equation

HRID 1750013 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]#[C:22][C:23]([N:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)([CH3:25])[CH3:24])=[C:19]([O:39][CH3:40])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]#[C:22][C:23]([CH3:24])([N:26]4[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]4)[CH3:25])=[C:19]([O:39][CH3:40])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487159HCID 178487159, compound

Product 1

HCID 178487158HCID 178487158, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-(4-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}-2-methylbut-3-yn-2-yl)piperazine-1-carboxylate (0.122 g, 0.225 mmol) in methylene chloride (4 mL) was added with trifluoroacetic acid (4 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and then the residue was dissolved in water (10 mL). The solution was added with saturated aqueous sodium hydrogencarbonate (10 mL), and the precipitated solid was collected by filtration. The solid was washed with water, and then dried under reduced pressure to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-7-[3-methyl-3-(piperazin-1-yl)but-1-ynyl]benzofuran-3(2H)-one (0.0259 g, 26%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water (10 mL)
  3. additionThe solution was added with saturated aqueous sodium hydrogencarbonate (10 mL)
  4. filtrationthe precipitated solid was collected by filtration
  5. washThe solid was washed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-3a0e7cb9fe73492b8527ea308b28c0ac
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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