Dichloromethane → HCID 86681969, compound

HRID 1749776Notes

Reaction equation

HRID 1749776 reaction equation
[OH:1][C:2]1[CH:34]=[CH:33][C:5]2[C:6](=[O:32])/[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]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:35][N:36]1[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]1.FC(F)(F)C(O)=O.C(Cl)[Cl:57]>>[ClH:57].[ClH:57].[OH:1][C:2]1[CH:34]=[CH:33][C:5]2[C:6](=[O:32])/[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]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[CH:11]=3)/[O:8][C:4]=2[C:3]=1[CH2:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86681968HCID 86681968, compound

Product 1

HCID 86681969HCID 86681969, compoundYield 64%

Procedure

A solution of tert-butyl (Z)-4-([6-hydroxy-3-oxo-2-({1-[4-(trifluoromethyl)phenylsulfonyl]-1H-indol-3-yl]methylene)-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.0500 g, 0.0731 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-7-(piperazin-1-ylmethyl)-2-({1-[4-(trifluoromethyl)phenylsulfonyl]-1H-indol-3-yl}methylene)benzofuran-3(2H)-one dihydrochloride (0.0311 g, 64%).

Workup

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

Sources & evidence

ORD record
ord-fd6ecd6d4d664fd8bad9607842a927b2
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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