2-Methoxyethylamine → 2-(4-Bromo-1H-pyrazol-1-yl)-N-(2-methoxyethyl)ethanamine

HRID 1942779Notes

Reaction equation

HRID 1942779 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Br:6][C:7]1[CH:8]=[N:9][N:10]([CH2:12][CH2:13]Cl)[CH:11]=1>CS(C)=O.CCOC(C)=O>[Br:6][C:7]1[CH:8]=[N:9][N:10]([CH2:12][CH2:13][NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 518920744-Bromo-1-(2-chloroethyl)-1H-pyrazole

Product 1

HCID 625656882-(4-Bromo-1H-pyrazol-1-yl)-N-(2-methoxyethyl)ethanamineYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methoxyethanamine (8.9 mL, 102.06 mmol) and chloride 75 (7.13 g, 34.02 mmol) in DMSO (20 mL) was heated at 60° C. 5 h. The mixture was then cooled to room temperature, diluted with EtOAc, washed with aqueous sodium bicarbonate, water and brine. The organic phase was further extracted with 1N HCl and the acid extract was collected and basified with 2N NaOH (pH˜11). The basic aqueous solution was extracted with DCM, the DCM extract was dried over anhydrous sodium sulphate, and concentrated under reduced pressure to afford title compound 76 (8.44 g, 99%) as brown foam. MS (m/z): 248.04 (M+H).

Workup

  1. custom5 h
  2. washwashed with aqueous sodium bicarbonate, water and brine
  3. extractionThe organic phase was further extracted with 1N HCl
  4. extractionthe acid extract
  5. customwas collected
  6. extractionThe basic aqueous solution was extracted with DCM
  7. extractionthe DCM extract
  8. dry with materialwas dried over anhydrous sodium sulphate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f79951fe4b284014a6f21bbc93085366
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Reaction notes

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