Water → HCID 178458174, compound

HRID 1749890Notes

Reaction equation

HRID 1749890 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][CH:36]([CH3:38])[CH3:37])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>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]([CH2:21][N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([O:35][CH:36]([CH3:38])[CH3:37])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178458176HCID 178458176, compound

Product 1

HCID 178458174HCID 178458174, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-6-isopropoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0740 g, 0.143 mmol) in methylene chloride (2 mL) was added with trifluoroacetic acid (2 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was added with water (6 mL) and saturated aqueous sodium hydrogencarbonate (6 mL), and thereby made basic, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was subjected to suction filtration, and the resulting solid was washed with water to obtain the objective (Z)-2-[(1H-indazol-3-yl)methylene]-6-isopropoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0301 g, 50%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. filtrationThe reaction mixture was subjected to suction filtration
  3. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-1163a6e331884abc878e35162772b368
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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