1-Methylpiperazine → HCID 85916567, compound

HRID 1395228Notes

Reaction equation

HRID 1395228 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[N:9][C:10]3[N:14]([CH2:15][CH3:16])[N:13]=[CH:12][C:11]=3[C:6]=2[N:5]2[N:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:4]2[N:3]=1.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(O)CCC>[CH2:15]([N:14]1[C:10]2[N:9]=[CH:8][C:7]3[C:2]([N:29]4[CH2:30][CH2:31][N:26]([CH3:25])[CH2:27][CH2:28]4)=[N:3][C:4]4[N:5]([N:17]=[CH:18][C:19]=4[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=3[C:11]=2[CH:12]=[N:13]1)[CH3:16]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 85916602HCID 85916602, compound

Product 1

HCID 85916567HCID 85916567, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

3.5 g of 5-chloro-8-ethyl-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester (0.01 mol) are dissolved in 20 ml of butanol. 2 g of N-methylpiperazine are added and the solution is refluxed with stirring for 12 hours. After evaporation of the solvent, the residue is extracted three times with 50 ml portions of ethyl acetate. The ethyl acetate is distilled off until the volume is about 30 ml. The 8-ethyl-5-(4-methyl-1-piperazinyl)-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester crystallizes, yield 3.1 g (76%); m.p. 111°-113° (ethyl acetate).

Workup

  1. temperaturethe solution is refluxed
  2. customAfter evaporation of the solvent
  3. extractionthe residue is extracted three times with 50 ml portions of ethyl acetate
  4. distillationThe ethyl acetate is distilled off until the volume
  5. customThe 8-ethyl-5-(4-methyl-1-piperazinyl)-8H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester crystallizes

Sources & evidence

ORD record
ord-a512dd637bdc4548b899d9fb087496a7
Source dataset
uspto-grants-1980_05
Patent number
US04202899

Reaction notes

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