Cesium carbonate → 5-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

HRID 1835124Notes

Reaction equation

HRID 1835124 reaction equation
[CH2:1]([C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([C:11]([NH2:13])=[O:12])[NH:5][N:4]=1)[CH3:2].[CH3:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:17][CH2:16][O:15][CH3:14])[N:5]=[C:6]([C:11]([NH2:13])=[O:12])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 178438045HCID 178438045, compound

Product 1

HCID 112187175-ethyl-1-(2-methoxyethyl)-4-nitro-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (1.62 g, 8.80 mmol, prepared using procedure in WO9849166), 2-bromoethyl methyl ether (1.23 g, 8.85 mmol) and cesium carbonate (2.90 g, 8.92 mmol) in N,N-dimethylformamide (20 ml) was stirred at 20° C. for 20 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc (125 ml) and brine (100 ml). The phases were separated, and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/MeOH, 97:3) to afford the title compound of preparation 4 (831 mg, 3.43 mmol, 39%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc (125 ml) and brine (100 ml)
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (EtOAc/MeOH, 97:3)
  8. customto afford

Sources & evidence

ORD record
ord-d41126499a414c74919360fe5259dc94
Source dataset
uspto-grants-2004_08
Patent number
US06770645B2

Reaction notes

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