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

HRID 432139Notes

Reaction equation

HRID 432139 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=8.5 Hz, 2H), 8.27 (s, 1H); LC/MS (MH+32 484).

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-3d8c58baad8b486ab4c757516110fc17
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…