Maleic Acid → HCID 131724236, compound

HRID 897427Notes

Reaction equation

HRID 897427 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20]4=[N:21][CH:22]=[N:23][C:24]([NH2:25])=[C:19]4[C:18]([C:26]4[CH:31]=[CH:30][C:29]([O:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:28][CH:27]=4)=[N:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43]>C(OCC)(=O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]\[C:42]([OH:44])=[O:43].[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20]4=[N:21][CH:22]=[N:23][C:24]([NH2:25])=[C:19]4[C:18]([C:26]4[CH:27]=[CH:28][C:29]([O:32][C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)=[CH:30][CH:31]=4)=[N:17]3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 22347030HCID 22347030, compound2×

Product 1

HCID 131724236HCID 131724236, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1-[1-(1-isopropyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate F) (132 mg, 0.258 mmol) was dissolved in 30 ml of hot ethyl acetate and maleic acid(90 mg, 0.774 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 205 mg of 1-[1-(1-isopropyl-4-piperidinyl)-4-piperidinyl]-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, trimaleate salt. 1H NMR (DMSO) 1.26(d, J=6.34 Hz, 6H), 1.90(m, 2H), 2.23(m, 4H), 2.50(m, 2H), 3.53(bm, 9H), 5.08(m, 1H), 7.16(m, 5H), 7.44(m, 2H), 7.67(d, J=8.30 Hz, 2H), 8.28(s, 1H); LC/MS (MH+=512)

Workup

  1. filtrationthe solid was filtered
  2. customdried

Sources & evidence

ORD record
ord-4262053df047458881b92e3b2e97eff0
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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