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

HRID 1838941Notes

Reaction equation

HRID 1838941 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

Procedure

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (WO, 9849166), (1.7 g, 8.8 mmol), 2-bromoethyl methyl ether (0.85 ml, 8.85 mmol) and cesium carbonate (2.9 g, 9.0 mmol) in N,N-dimethylformamide (20 ml) was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (125 ml) and brine (100 ml). The phases were separated, and the organic layer was dried (Na2SO4), and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using ethyl acetate:methanol (97:3) as eluant to afford the title compound of preparation 1,831 mg,

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate (125 ml) and brine (100 ml)
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel
  7. customto afford

Sources & evidence

ORD record
ord-453d263501f34ac6b5296b7a5bfb18ff
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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