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

HRID 897430Notes

Reaction equation

HRID 897430 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:22])=[C:16]4[C:15]([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)=[N:14]3)[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40]>C(O)C>[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[C:36]([OH:43])(=[O:42])/[CH:37]=[CH:38]\[C:39]([OH:41])=[O:40].[NH:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:17]4=[N:18][CH:19]=[N:20][C:21]([NH2:22])=[C:16]4[C:15]([C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)=[N:14]3)[CH2:9][CH2:8]2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 223469961-[1-(4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 1317242371-[1-(4-piperidyl)-4-piperidyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate saltYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-[1-(4-piperidyl)-4-piperidyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (108 mg, 0.230 mmol) was dissolved in 25 ml of ethanol and maleic acid (80 mg, 0.690 mmol) in 5 ml of hot ethanol was added. After 2 hours at room temperature, the solid was filtered and dried to give 155 mg of 1-[1-(4-piperidyl)-4-piperidyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate salt. 1H NMR (DMSO) 1.80(m, 2H), 2.42(m, 4), 2.51(m, 2H), 2.95(m, 3H), 3.44(bm, 7H), 5.06(m, 1H), 6.10 (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+=484).

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-462dc5d1a4a34c2f96dfc480a59653ab
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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