Potassium Carbonate → HCID 68830562, compound

HRID 1727368Notes

Reaction equation

HRID 1727368 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:21]3[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH2:19]O)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:33])=O.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O>[ClH:33].[ClH:33].[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([C:10]2[S:11][C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH:14]=3)=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)[N:9]=2)=[CH:22][CH:23]=1)(=[O:28])=[O:29]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 53426476(4-{2-[4-(Methanesulfonyl)phenyl]-4-(3-methylphenyl)-1,3-thiazol-5-yl}pyridin-2-yl)methanol

Product 1

HCID 68830562HCID 68830562, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(3-methylphenyl)-2-(4-methylsulfonylphenyl)-1,3-thiazol-5-yl]-2-pyridylmethanol (0.43 g, 1.0 mmol) in tetrahydrofuran (20 mL) was added thionyl chloride (0.08 mL, 1.0 mmol), and the mixture was stirred for 20 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was added to a suspension of pyrrolidine (0.09 mL, 1.1 mmol) and potassium carbonate (0.36 g, 2.6 mmol) in N,N-dimethylformamide (10 mL), and the mixture was stirred for 27 hours at room temperature. To the mixture was added an aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, and filtrated and concentrated under reduced pressure. The residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:2). The resulted oil was dissolved in methanol (10 mL), and to this was added a 10% hydrogen chloride-methanol solution (5 mL), and the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the resulting solid was washed with ethanol, to obtain a title compound (yield 17%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe mixture was stirred for 27 hours at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (filler: Chromatorex NH DM1020 (trade name, manufactured by Fuji Silysia Chemical Ltd.), hexane-ethyl acetate=1:2)
  9. dissolutionThe resulted oil was dissolved in methanol (10 mL)
  10. additionto this was added a 10% hydrogen chloride-methanol solution (5 mL)
  11. stirringthe mixture was stirred for 1 hour at room temperature
  12. concentrationThe reaction mixture was concentrated under reduced pressure
  13. washthe resulting solid was washed with ethanol

Sources & evidence

ORD record
ord-c61ed2fc0c8a49f69a6ae6dcc834d9ac
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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