Trifluoroacetic acid → HCID 178515794, compound

HRID 1749892Notes

Reaction equation

HRID 1749892 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]([CH2:21][N:22]4[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[C:19]([O:35][CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[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]([CH2:21][N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([O:35][CH2:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178452315HCID 178452315, compound

Product 1

HCID 178515794HCID 178515794, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-3-oxo-6-phenethoxy-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0730 g, 0.126 mmol) in methylene chloride (3 mL) was added with trifluoroacetic acid (3 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated, added with methanol (8 mL) and a 5% solution of hydrogen chloride in methanol (2 mL), and thereby made basic, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, and then the residue was suspended in acetonitrile and thereby washed to obtain an orange solid. This solid was suspended in water (4 mL) and saturated aqueous sodium hydrogencarbonate (4 mL), and the suspension was stirred for 1 hour. The reaction mixture was filtered, and then the resulting solid was washed with water to obtain the objective (Z)-2-[(1H-indazol-3-yl)methylene]-6-phenethoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0211 g, 34%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with methanol (8 mL)
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. concentrationThe reaction mixture was concentrated
  5. washwashed
  6. customto obtain an orange solid
  7. filtrationThe reaction mixture was filtered
  8. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-9d1937eda360464a8b0f32f7219667fe
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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