Dichloromethane → HCID 86681963, compound
Reaction equation
[OH:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6](=[O:23])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:26][N:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]1.FC(F)(F)C(O)=O.C(Cl)[Cl:48]>>[ClH:48].[ClH:48].[OH:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6](=[O:23])/[C:7](=[CH:9]/[C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([S:19]([CH3:22])(=[O:20])=[O:21])[CH:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1Participants
Procedure
A solution of tert-butyl (Z)-4-[(6-hydroxy-2-{[1-(methylsulfonyl)-1H-indol-3-yl]methylene}-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0500 g, 0.0903 mmol) in methylene chloride (2 mL) was added with trifluoroacetic acid (2 mL), and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, then a solution of the resulting residue in methanol (4 mL) was added with a 5% solution of hydrogen chloride in methanol (1 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 the objective (Z)-6-hydroxy-2-{[1-(methylsulfonyl)-1H-indol-3-yl]methylene}-7-(piperazin-1-ylmethyl)benzofuran-3(2H)-one dihydrochloride (0.0421 g, 88%).
Workup
- concentrationThe reaction mixture was concentrated
- additiona solution of the resulting residue in methanol (4 mL) was added with a 5% solution of hydrogen chloride in methanol (1 mL)
- stirringthe mixture was stirred at room temperature for 2 hours
- customThe solvent was evaporated
- washwashed
Sources & evidence
- ORD record
- ord-35185690d42242f3959d444a556a5e08
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
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