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Triethylamine → 3-(3,5-Difluorophenyl)-6-(3-(4-(methylsulfonyl)piperazin-1-yl)propoxy)-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331318
Notes
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Reaction equation

HRID 331318 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][CH:32]=[CH:33][CH:34]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[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][N:25]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:24][CH2:23]4)=[CH:15][CH:16]=3)[C:11](=[O:28])[C:10]=2[C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH:5]=[C:6]([F:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 510019386-(3-(piperazin-1-yl)propoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 510019413-(3,5-Difluorophenyl)-6-(3-(4-(methylsulfonyl)piperazin-1-yl)propoxy)-2-(pyridin-3-yl)-1H-inden-1-oneYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Conditions

Temperature
0 °C

Procedure

To a 10 mL round-bottomed flask, 6-(3-(piperazin-1-yl)propoxy)-3-(3,5-difluorophenyl)-2-(pyridin-3-yl)-1H-inden-1-one (30 mg, 1.2 eq) obtained in Step 1 of Example 66 and CH2Cl2 (1 mL, 0.05M) were charged. Triethylamine (0.02 mL, 1.5 eq) was added and then the mixture was cooled to 0° C. and treated with a solution of methylsulfonyl chloride (6.2 mg, 0.05 mmol) in CH2Cl2 (1 mL) over 5 min. After being stirred for 3 h, the mixture was diluted with CH2Cl2 and washed with H2O and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (CH2Cl2/MeOH=9:1) and being purified by prep. HPLC (20% H2O/CH3CN) to provide the title compound (19.8 mg, 68%).

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2/MeOH=9:1)
  5. custombeing purified by prep

Sources & evidence

ORD record
ord-7d1e8cd29199465d961aa709d89fb7ea
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877747B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes