2-(Dimethylamino)ethanol → HCID 117839748, compound

HRID 1477707Notes

Reaction equation

HRID 1477707 reaction equation
CN(CCO)C.[Cl:7][C:8]1[CH:27]=[CH:26][C:11]([CH2:12][N:13]2[CH:18]=[N:17][C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:15][C:14]2=[O:25])=[CH:10][CH:9]=1.Br[C:29]1[S:30][C:31]([Cl:34])=[CH:32][CH:33]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu].[Cu]I.C(OCC)(=O)C.CCOCC.O>[Cl:7][C:8]1[CH:27]=[CH:26][C:11]([CH2:12][N:13]2[CH:18]=[N:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:29]4[S:30][C:31]([Cl:34])=[CH:32][CH:33]=4)[CH2:21][CH2:20]3)=[N:15][C:14]2=[O:25])=[CH:10][CH:9]=1

Participants

10

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 62657Potassium Phosphate, TribasicHCID 761332-Bromo-5-chlorothiopheneHCID 117839396HCID 117839396, compound

Product 1

HCID 117839748HCID 117839748, compoundYield 1.2%

Reagents, catalysts & solvents 5

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

An N,N-dimethylaminoethanol suspension (1 mL) of 1-(4-chlorobenzyl)-4-(piperazin-1-yl)-1,3,5-triazin-2(1H)-one (30 mg, 0.10 mmol) synthesized in Reference Synthesis Example 9, 2-bromo-5-chlorothiophene (110 μL, 0.10 mmol), copper (3.0 mg, 0.05 mmol), copper (I) iodide (9 mg, 0.05 mmol), and potassium phosphate (43 mg, 0.20 mmol) was stirred at 80° C. for 3 days. After the completion of the reaction, water was added to the reaction solution and extraction with ether and ethyl acetate from the resultant reaction solution was performed. The organic layer was washed with brine, was dried over anhydrous sodium sulfate, and was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/methanol) to obtain the title compound (0.5 mg, yield: 1.2%).

Workup

  1. customreaction solution
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationwas concentrated under reduced pressure
  5. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-0335a5677ef94077b6f1ecc7d8f0ee69
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

Loading…