Maleic Acid → HCID 178481013, compound

HRID 432179Notes

Reaction equation

HRID 432179 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:18]4=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]4[C:16]([C:24]4[CH:25]=[N:26][C:27]([O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[N:28][CH:29]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41]>C(O)C>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]\[C:40]([OH:42])=[O:41].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:18]4=[N:19][CH:20]=[N:21][C:22]([NH2:23])=[C:17]4[C:16]([C:24]4[CH:25]=[N:26][C:27]([O:30][C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[N:28][CH:29]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178481012HCID 178481012, compound

Product 1

HCID 178481013HCID 178481013, compoundYield 171.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of trans-1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Int AX) (0.155 g, 0.00032 mol) in absolute ethanol (15 mL) was heated to reflux. A solution of maleic acid (0.148 g, 0.000128 mol) in absolute ethanol (10 mL) heated to 78° C. was added and the mixture was heated at reflux for 10 minutes. The mixture was allowed to cool to room temperature, and the white precipitate which formed was collected by filtration and washed with absolute ethanol (2×10 mL). The residual solvent was removed in vacuo to give trans-1-[4-(4-methylpiperazino)cyclohexyl]-3-(2-phenoxy-5-pyrimidinyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine bis maleate as a white solid (0.082 g, 0.00011 mol):

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 10 minutes
  4. customthe white precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with absolute ethanol (2×10 mL)
  7. customThe residual solvent was removed in vacuo

Sources & evidence

ORD record
ord-71a0b2e9a40342c780a288c87247a86c
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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