Dimethylformamide → HCID 89726608, compound

HRID 1777749Notes

Reaction equation

HRID 1777749 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1.[CH3:13][N:14]([CH:16]=O)[CH3:15]>CC#N.C(Cl)Cl>[CH3:13][N:14]([CH2:16][C:6]1[C:2]([CH3:1])=[N:3][N:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:5]=1)[CH3:15]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 4578874Ethyl 3-methyl-1H-pyrazole-1-acetate

Product 1

HCID 89726608HCID 89726608, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl 2-(3-methyl-1H-pyrazol-1-yl)acetate (94 mg) and DMF (1.5 mL) in MeCN (3 mL) was added N,N-dimethylmethyleneiminium iodide (390 mg). The reaction mixture was stirred at 90° C. overnight. After cooling down, the reaction mixture was diluted with DCM and washed with sat. NaHCO3 and water. The aq. layers were extracted with DCM, the combined org. layers were dried (MgSO4), filtered off and evaporated in vacuo to afford ethyl 2-(4-((dimethylamino)methyl)-3-methyl-1H-pyrazol-1-yl)acetate (112 mg, brown oil). LC-MS (B): tR=0.39 min; [M+H]+: 226.23.

Workup

  1. temperatureAfter cooling down
  2. washwashed with sat. NaHCO3 and water
  3. extractionThe aq. layers were extracted with DCM
  4. dry with materiallayers were dried (MgSO4)
  5. filtrationfiltered off
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ffdcf79c05774a38bedd7ea44b5672a8
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

Loading…