Triethylamine → 3-(3,5-Difluorophenyl)-2-(6-methoxypyridin-3-yl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-inden-1-one

HRID 331364Notes

Reaction equation

HRID 331364 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:28])[C:10]=2[C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([C:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH2:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][N:25]([S:45]([CH3:44])(=[O:47])=[O:46])[CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:28])[C:10]=2[C:29]2[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 703137133-(3,5-Difluorophenyl)-2-(6-methoxypyridin-3-yl)-6-(3-(piperazin-1-yl)propoxy)-1H-inden-1-one

Product 1

HCID 681814383-(3,5-Difluorophenyl)-2-(6-methoxypyridin-3-yl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-inden-1-oneYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3,5-difluorophenyl)-2-(6-methoxypyridin-3-yl)-6-(3-(piperazin-1-yl)propoxy)-1H-inden-1-one (90 mg, 1.2 eq, 0.2 mmol) obtained in Step 2 in CH2Cl2 at 0° C. was added triethylamine (1.5 eq) and methylsulfonyl chloride (1.0 eq). The mixture was stirred for 1 h at room temperature and diluted with CH2Cl2. The mixture was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1) to obtain the title compound (20%).

Workup

  1. washThe mixture was washed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:1)

Sources & evidence

ORD record
ord-9f5bf44f36154e7ca05441f620879c53
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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