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Maleic Acid → HCID 178480995, compound

HRID 432168
Notes
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Reaction equation

HRID 432168 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:25]=[N:26][C:27]([O:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:28][CH:29]=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(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:25]=[N:26][C:27]([O:30][C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)=[CH:28][CH:29]=4)=[N:15]3)[CH2:10][CH2:9]2)[CH2:6][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 178480994HCID 178480994, compound

Product 1

HCID 178480995HCID 178480995, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate AJ) (0.53 g, 0.0011 mol) in a mixture of ethyl acetate (25 mL) and ethanol (4 mL) was heated at reflux and a preheated solution of maleic acid (0.51 g, 0.0044 mol) in ethyl acetate (15 mL) was added. The mixture was refluxed for another 10 min, cooled to ambient temperature and the precipitate collected by filtration, washed with ethyl acetate and dried to yield cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo [3,4-d]pyrimidin-4-amine dimaleate as a white solid (0.61 g, 0.00084 mol): 1H NMR (DMSO-d6, 400 MHz) 8.38 (s, 1H), 8.25 (s, 1H), 8.06 (d, 1H), 7.46 (t, 2H), 7.22 (m, 4H), 6.15 (s, 4H), 4.85 (m, 1H), 3.1 (br, 9H), 2.70 (s, 3H), 2.25 (m, 2H), 2.04 (m, 2H), 1.74 (m, 4H); RP-HPLC (Delta Pak C18, 5 μm, 300A, 15 cm; 5%-85% acetonitrile-0.1M ammonium acetate over 20 min, 1 mL/min) Rt 11.93 min. MS: MH+485.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe mixture was refluxed for another 10 min
  4. filtrationthe precipitate collected by filtration
  5. washwashed with ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-cc1232416ae8428bb08c191772e9ec0a
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06660744B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes