Trifluoroacetic acid → HCID 178515795, compound

HRID 1749895Notes

Reaction equation

HRID 1749895 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][O:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[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]([CH2:21][N:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]4)=[C:19]([O:35][CH2:36][CH2:37][O:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178452320HCID 178452320, compound

Product 1

HCID 178515795HCID 178515795, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indazol-3-yl)methylene]-3-oxo-6-(2-phenoxyethoxy)-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0380 g, 0.0637 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 concentrated, and added with water (4 mL) and saturated aqueous sodium hydrogencarbonate (4 mL), and the mixture 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-(2-phenoxyethoxy)-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0280 g, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with water (4 mL) and saturated aqueous sodium hydrogencarbonate (4 mL)
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationThe reaction mixture was filtered
  5. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-c618a443f71544ae9e95a660b4a47d90
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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