Trifluoroacetic acid → HCID 178487224, compound

HRID 1749885Notes

Reaction equation

HRID 1749885 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)=[C:20]([O:36][CH3:37])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2/[CH:11]=[C:12]1\[O:13][C:14]2[C:21]([CH2:22][N:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)=[C:20]([O:36][CH3:37])[CH:19]=[CH:18][C:15]=2[C:16]\1=[O:17]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178487230HCID 178487230, compound

Product 1

HCID 178487224HCID 178487224, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(5-bromo-1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.160 g, 0.281 mmol) in methylene chloride (4 mL) was added with trifluoroacetic acid (4 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was concentrated, and then added with water (10 mL) and saturated aqueous sodium hydrogencarbonate (10 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and then the resulting solid was washed with water to obtain the objective (Z)-2-[(5-bromo-1H-indazol-3-yl)methylene]-6-methoxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one (0.0860 g, 65%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionadded with water (10 mL) and saturated aqueous sodium hydrogencarbonate (10 mL)
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. filtrationThe reaction mixture was filtered
  5. washthe resulting solid was washed with water

Sources & evidence

ORD record
ord-2a8b15051cc34c10a94b02a5eda78e1b
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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