Trifluoroacetic acid → HCID 86681983, compound

HRID 1749787Notes

Reaction equation

HRID 1749787 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](/[CH:21]=[C:22]2\[O:23][C:24]3[C:31]([CH2:32][N:33]4[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]4)=[C:30]([OH:46])[CH:29]=[CH:28][C:25]=3[C:26]\2=[O:27])=[CH:13]1)(=[O:11])=[O:10].FC(F)(F)C(O)=O>C(Cl)Cl>[ClH:1].[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](/[CH:21]=[C:22]2\[O:23][C:24]3[C:31]([CH2:32][N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[C:30]([OH:46])[CH:29]=[CH:28][C:25]=3[C:26]\2=[O:27])=[CH:13]1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681985HCID 86681985, compound

Product 1

HCID 86681983HCID 86681983, compoundYield 180.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (Z)-4-[(2-{[1-(2,3-dichlorophenylsulfonyl)-1H-indol-3-yl]methylene}-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.152 g, 0.222 mmol) in methylene chloride (6 mL) was added with trifluoroacetic acid (6 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, then a solution of the resulting residue in methanol (8 mL) was added with a 5% solution of hydrogen chloride in methanol (2 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated, and the resulting solid was suspended in acetonitrile and thereby washed to obtain (Z)-2-{[1-(2,3-dichlorophenylsulfonyl)-1H-indol-3-yl]methylene}-6-hydroxy-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride (0.0878 g, 60%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiona solution of the resulting residue in methanol (8 mL) was added with a 5% solution of hydrogen chloride in methanol (2 mL)
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. customThe solvent was evaporated
  5. washwashed

Sources & evidence

ORD record
ord-79d03f3c0b2e4175bd2ec2b1256b9875
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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