2-Aminomethyl-1-ethylpyrrolidine → 6-chloro-5-(ethylamino)-N-[(1-ethylpyrrolidin-2-yl)methyl]-3-methoxypyrazine-2-carboxamide

HRID 441497Notes

Reaction equation

HRID 441497 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=O)[C:5]([O:12][CH3:13])=[N:4][C:3]=1[NH:14][CH2:15][CH3:16].[NH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][CH3:25]>CO>[CH2:24]([N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][NH:17][C:8]([C:6]1[C:5]([O:12][CH3:13])=[N:4][C:3]([NH:14][CH2:15][CH3:16])=[C:2]([Cl:1])[N:7]=1)=[O:10])[CH3:25]

Participants

4

Reactant 2

HCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 21418994Methyl 5-ethylamino-6-chloro-3-methoxypyrazine-2-carboxylate

Product 1

HCID 159428306-chloro-5-(ethylamino)-N-[(1-ethylpyrrolidin-2-yl)methyl]-3-methoxypyrazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml. of methanol were dissolved 2.0 g. of methyl 6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxylate and 2.0 g. of 2-aminomethyl-1-ethylpyrrolidine and the solution was refluxed for 24 hours. After cooling, the solvent was distilled off under reduced pressure from the reaction mixture to provide an oily residue. The residue was dissolved in 30 ml. of a dilute aqueous hydrochloric acid solution and the solution was washed three times each time with 10 ml. of chloroform. (The chloroform washings was washed with water, dried, and then the solvent was distilled off under reduced pressure, whereby 1.05 g. of methyl 6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxylate used as the starting material was recovered.). The aqueous layer was basified with a 3 N aqueous sodium hydroxide solution and the oily material formed was extracted with 30 ml. of chloroform. The extract was washed with water, dried, the solvent was distilled off under reduced pressure, and the oily residue formed was allowed to stand, whereby the oily residue was crystallized. After recrystallizing the crystals from toluene, 0.88 g. of N-(1-ethylpyrrolidin-2-ylmethyl)-6-chloro-5-ethylamino-3-methoxypyrazine-2-carboxamide melting at 167°-169° C. was obtained.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled off under reduced pressure from the reaction mixture
  3. customto provide an oily residue
  4. dissolutionThe residue was dissolved in 30 ml
  5. washof a dilute aqueous hydrochloric acid solution and the solution was washed three times each time with 10 ml
  6. wash(The chloroform washings was washed with water
  7. customdried
  8. distillationthe solvent was distilled off under reduced pressure, whereby 1.05 g
  9. customwas recovered
  10. customthe oily material formed
  11. extractionwas extracted with 30 ml
  12. washThe extract was washed with water
  13. customdried
  14. distillationthe solvent was distilled off under reduced pressure
  15. customthe oily residue formed
  16. customwhereby the oily residue was crystallized
  17. customAfter recrystallizing the crystals from toluene, 0.88 g

Sources & evidence

ORD record
ord-b46c292d71e34720825eecc2b0d19073
Source dataset
uspto-grants-1977_08
Patent number
US04041032

Reaction notes

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