Potassium Hydroxide → 8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-1,4,4-trimethyl-4,5-dihydro-1h-pyrazolo[4,3-h]quinazoline-3-carboxylic acid potassium salt

HRID 44630Notes

Reaction equation

HRID 44630 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]3[N:24]=[CH:23][C:22]4[CH2:21][C:20]([CH3:26])([CH3:25])[C:19]5[C:27]([C:31]([O:33]CC)=[O:32])=[N:28][N:29]([CH3:30])[C:18]=5[C:17]=4[N:16]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[OH-].[K+:37]>C(O)C>[K+:37].[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]3[N:24]=[CH:23][C:22]4[CH2:21][C:20]([CH3:26])([CH3:25])[C:19]5[C:27]([C:31]([O-:33])=[O:32])=[N:28][N:29]([CH3:30])[C:18]=5[C:17]=4[N:16]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 57531723HCID 57531723, compound

Product 1

HCID 689345638-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-1,4,4-trimethyl-4,5-dihydro-1h-pyrazolo[4,3-h]quinazoline-3-carboxylic acid potassium salt

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of ethyl 8-[4-(4-methyl-piperazin-1-yl)-phenylamino]-1,4,4-trimethyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (11.60 g, 24.390 mmol) in anhydrous ethanol (450 mL), 1.5 M potassium hydroxide in 95% ethanol (63 mL) was added under good stirring and the mixture was heated to reflux for 3 hours. After cooling in an ice bath, a solid was formed, that was filtered washing with ethanol, dried at 40° C. under vacuum to yield 11.8 g (quantitative yield) of white solid title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. temperatureAfter cooling in an ice bath
  5. customa solid was formed
  6. filtrationthat was filtered
  7. washwashing with ethanol
  8. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-d39a7685bfff439fb8b6aa42e9b2da0d
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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