Cesium carbonate → HCID 23503220, compound

HRID 1835128Notes

Reaction equation

HRID 1835128 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].Cl[CH2:15][C:16]1[N:17]=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH2:1]([C:3]1[N:4]([CH2:15][C:16]2[N:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[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 142397123-(Chloromethyl)pyridazineHCID 178438045HCID 178438045, compound

Product 1

HCID 23503220HCID 23503220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (15.7 g, 85.6 mmol, prepared using procedure in WO9849166), 3-(chloromethyl)pyridazine (11.0 g, 85.6 mmol, prepared using procedure in WO0023449) and cesium carbonate (27.8 g, 85.6 mmol) in N,N-dimethylformamide (200 ml) was stirred at 20° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between DCM (200 ml) and 10% aqueous Na2CO3 (100 ml). The phases were separated, and the aqueous layer extracted with further DCM (6×50 ml). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/MeOH, 95:5-9010) to afford the title compound of preparation 43 (Note, the regioisomers were assigned on the basis of nOe experiments) (4.09 g, 14.8 mmol, 17%):

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was partitioned between DCM (200 ml) and 10% aqueous Na2CO3 (100 ml)
  4. customThe phases were separated
  5. extractionthe aqueous layer extracted with further DCM (6×50 ml)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (EtOAc/MeOH, 95:5-9010)
  10. customto afford

Sources & evidence

ORD record
ord-70f4d82e179b4668ba95bd4cb83c53c7
Source dataset
uspto-grants-2004_08
Patent number
US06770645B2

Reaction notes

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