Maleic Acid → HCID 178480992, compound

HRID 432142Notes

Reaction equation

HRID 432142 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:29]=[CH:28][C:27]([O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:26][CH:25]=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[CH2:3][CH2:4][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:29]=[CH:28][C:27]([O:30][C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:26][CH:25]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 178480991HCID 178480991, compound

Product 1

HCID 178480992HCID 178480992, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Trans-1-(4-(4-methylpiperazino)cyclohexyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.47 g, 0.972 mmol) was dissolved in 140 ml of hot ethanol and maleic acid (0.40 g, 2.47 mmol) in 10 ml of hot ethanol was added. After 2 hours at room temperature, the solid was filtered and then dried to give 0.62 g of 1-(trans-4-(4-methylpiperazino)cyclohexyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, dimaleate salt. 1H NMR (DMSO) 1.58(m, 2H), 2.04 (m, 6), 2.67 (m, 3H), 2.79(vbm, 9H), 4.70 (m, 1H), 7.41 (s, 4H), 7.17 (m, 5H), 7.44 (m, 2H), 7.66 (d, J=8.63 Hz, 2H), 8.24 (s, 1H); LC/MS (MH+32 484).

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-57dcac6994f743e3bc8db9c1759e96bb
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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