1-Methylpiperazine → HCID 85916567, compound

HRID 224624Notes

Reaction equation

HRID 224624 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[1,5a]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[1,5a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidine-3-carboxylic acid, ethyl ester crystallizes

Sources & evidence

ORD record
ord-615466748834421a861f5519328ddaa7
Source dataset
uspto-grants-1980_11
Patent number
US04233300

Reaction notes

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