Dimethylformamide → HCID 67196893, compound

HRID 547510Notes

Reaction equation

HRID 547510 reaction equation
[CH2:1]([O:3][C:4]([C:6]1(N)[CH:10]=[CH:9][NH:8][NH:7]1)=[O:5])[CH3:2].Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:28](C)C=O>>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([NH2:28])[N:8]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7666Phenethyl bromideHCID 10796Cesium carbonateHCID 67194462HCID 67194462, compound

Product 1

HCID 67196893HCID 67196893, compoundYield 35%

Procedure

200 mg (1.3 mM) of 3-amino-1H-pyrazole-3-carboxylic acid ethyl ester was dissolved in 3 ml of N,N-dimethylformamide, to which 0.21 ml (1.6 mM, 1.2 eq) of 2-bromoethylbenzene and 840 mg (2.6 mM, 2.0 eq) of cesium carbonate were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for a day. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=4:1), to obtain 117 mg (35.0%) of the title compound.

Workup

  1. additionwere added dropwise
  2. distillationThe solvent was distilled off under reduced pressure
  3. extractionthe resultant was extracted with ethyl acetate and brine
  4. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f45666fc3b384b058f94d5ed180eb070
Source dataset
uspto-grants-2011_05
Patent number
US07939550B2

Reaction notes

Loading…