1,1'-Carbonyldiimidazole → N-[(1-ethyl-2-pyrrolidinyl) methyl]-5-methoxy-1,3-dimethylpyrazole-4-carboxamide

HRID 903153Notes

Reaction equation

HRID 903153 reaction equation
[CH3:1][N:2]1[C:6]([O:7][CH3:8])=[C:5]([C:9](O)=[O:10])[C:4]([CH3:12])=[N:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:32][CH3:33]>CN(C)C=O.O1CCCC1>[CH2:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][NH:25][C:9]([C:5]1[C:4]([CH3:12])=[N:3][N:2]([CH3:1])[C:6]=1[O:7][CH3:8])=[O:10])[CH3:33]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 233617795-methoxy-1,3-dimethyl-1H-pyrazole-4-carboxylic acid

Product 1

HCID 54397341N-[(1-ethyl-2-pyrrolidinyl) methyl]-5-methoxy-1,3-dimethylpyrazole-4-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.1 g (0.0178 mole) of 1,3-dimethyl-5-methoxy-4-pyrazole carboxylic acid was dissolved in 15 ml of dry N,N-dimethylformamide. Then 3.18 g (0.0196 mole) of 1,1'-carbonyl-diimidazole was added. The reaction mixture was stirred for one hour. A solution of 2.28 g (0.0178 mole) of 2-(aminomethyl)-1-ethylpyrrolidine in 10 ml of dry tetrahydrofuran was added dropwise with stirring over 1/2 hour. The reaction was then stirred overnight at room temperature and the solvent evaporated under vacuum (1 mm) and a water bath (60° C.). The resultant oil was then taken up in chloroform, washed with a saturated solution of sodium chloride, dried over sodium sulfate and evaporated. 4.5 g of amber colored oil (90% yield) was obtained.

Workup

  1. stirringwith stirring over 1/2 hour
  2. stirringThe reaction was then stirred overnight at room temperature
  3. customthe solvent evaporated under vacuum (1 mm) and a water bath (60° C.)
  4. washwashed with a saturated solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-52a1ed3101d744c0a0e45307d4c119ff
Source dataset
uspto-grants-1980_10
Patent number
US04226877

Reaction notes

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