Potassium Carbonate → (3-(4-(Pyrimidin-2-yl)piperazin-1-yl)azetidin-1-yl)(6-(trifluoromethyl)benzo[b]thiophen-2-yl)methanone

HRID 1961375Notes

Reaction equation

HRID 1961375 reaction equation
[N:1]1([CH:7]2[CH2:10][N:9]([C:11]([C:13]3[S:17][C:16]4[CH:18]=[C:19]([C:22]([F:25])([F:24])[F:23])[CH:20]=[CH:21][C:15]=4[CH:14]=3)=[O:12])[CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:27]1[N:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[N:28]1[CH:29]=[CH:30][CH:31]=[N:32][C:27]=1[N:4]1[CH2:5][CH2:6][N:1]([CH:7]2[CH2:10][N:9]([C:11]([C:13]3[S:17][C:16]4[CH:18]=[C:19]([C:22]([F:23])([F:25])[F:24])[CH:20]=[CH:21][C:15]=4[CH:14]=3)=[O:12])[CH2:8]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 783452-BromopyrimidineHCID 66770300(3-(Piperazin-1-yl)azetidin-1-yl)(6-(trifluoromethyl)benzo[b]thiophen-2-yl)methanone

Product 1

HCID 59626169(3-(4-(Pyrimidin-2-yl)piperazin-1-yl)azetidin-1-yl)(6-(trifluoromethyl)benzo[b]thiophen-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (3-(piperazin-1-yl)azetidin-1-yl)(6-(trifluoromethyl)benzo[b]thiophen-2-yl)methanone (0.14 mmol, 50 mg), 2-bromopyrimidine (0.23 mmol, 37 mg), and K2CO3 (0.34 mmol, 47 mg) in THF (3 mL) and water (1.5 mL) was refluxed for 8 h. Following workup and extraction, the residue was purified by flash column chromatography (silica gel, 3% methanol/CH2Cl2) to yield (3-(4-(pyrimidin-2-yl)piperazin-1-yl)azetidin-1-yl)(6-(trifluoromethyl)benzo[b]thiophen-2-yl)methanone as a white solid.

Workup

  1. temperaturewas refluxed for 8 h
  2. extractionworkup and extraction
  3. customthe residue was purified by flash column chromatography (silica gel, 3% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-92ee9e7b718a4afbb62e12c36e88200d
Source dataset
uspto-grants-2013_04
Patent number
US08415341B2

Reaction notes

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