Maleic Acid → 1-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate salt

HRID 432134Notes

Reaction equation

HRID 432134 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:13][CH2:12][CH: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(OCC)(=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].[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][CH:5]([N:8]2[CH2:13][CH2:12][CH: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)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 223470911-[1-(1-methyl-4-piperidinyl)-4-piperidinyl](4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1317242351-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate saltYield 85.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (92 mg, 0.190 mmol) was dissolved in 25 ml of hot ethyl acetate and maleic acid(66 mg, 0.571 mmol) in 5 ml of hot ethyl acetate was added. After 2 hours at room temperature, the solid was filtered and then dried to give 135 mg of 1-[1-(1-methyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate salt. 1H NMR (DMSO) 1.87 (m, 2H), 2.22 (m, 4), 2.45 (m, 2H), 2.77 (s, 3H), 2.18 (m, 9H), 5.06 (m, 1H), 6.11 (s, 6H), 7.15(m, 5H), 7.45 (m, 2H), 7.67 (d, J=8.51 Hz, 2H), 8.27 (s, 1H); LC/MS (MH+32 484).

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-c7370bf91abf48299252bbbf57880ace
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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