Potassium Carbonate → HCID 67463903, compound

HRID 1429561Notes

Reaction equation

HRID 1429561 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([CH2:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([CH2:9][CH:10]3[CH2:11][CH2:12][N:13]([C:19]4[N:24]=[CH:23][C:22]([CH2:25][CH2:26][CH3:27])=[CH:21][N:20]=4)[CH2:14][CH2:15]3)[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27357842-Chloro-5-propylpyrimidineHCID 67467025HCID 67467025, compound

Product 1

HCID 67463903HCID 67463903, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-2-(piperidin-4-ylmethyl)benzo[d]thiazole (380 mg, 1.221 mmol) and 2-chloro-5-propylpyrimidine (249 mg, 1.587 mmol) in DMF (8 mL) was added potassium carbonate (675 mg, 4.88 mmol). The reaction mixture was stirred at 110° C. for 3 h. The reaction mixture was cooled to rt, diluted with water (15 mL), and extracted with EtOAc (3×10 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude product was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc) to afford 6-bromo-2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]thiazole (252 mg, 0.584 mmol, 48% yield) as a light brown solid. LCMS (m/z)=432 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 50% EtOAc)

Sources & evidence

ORD record
ord-6d673036e948457ca3066de046df81d2
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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