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5-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester → 1-{4-[3-Phenyl-8-(1H-pyrazol-5-yl)pyrimido[1,2-b]indazol-2-yl]phenyl}-cyclobutylamine

HRID 877073
Notes
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Reaction equation

HRID 877073 reaction equation
C(OC([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]3[C:20]([CH:21]=2)=[N:19][N:18]2[CH:22]=[C:23]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:24]([C:26]4[CH:31]=[CH:30][C:29]([C:32]5([NH:36]C(OC(C)(C)C)=O)[CH2:35][CH2:34][CH2:33]5)=[CH:28][CH:27]=4)=[N:25][C:17]=32)=[CH:11][CH:10]=[N:9]1)=O)(C)(C)C>Cl.O1CCOCC1>[C:44]1([C:23]2[C:24]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4([NH2:36])[CH2:35][CH2:34][CH2:33]4)=[CH:30][CH:31]=3)=[N:25][C:17]3[N:18]([CH:22]=2)[N:19]=[C:20]2[C:16]=3[CH:15]=[CH:14][C:13]([C:12]3[NH:8][N:9]=[CH:10][CH:11]=3)=[CH:21]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 679912345-[2-(4-{1-[(Tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester

Product 1

HCID 573787511-{4-[3-Phenyl-8-(1H-pyrazol-5-yl)pyrimido[1,2-b]indazol-2-yl]phenyl}-cyclobutylamineYield 22.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

206.7 mg Crude 5-[2-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-3-phenylpyrimido[1,2-b]indazol-8-yl]pyrazole-1-carboxylic acid tert-butyl ester, intermediate example Int-3-0, were dissolved in 15 mL 4 M hydrogen chloride in dioxane. The reaction mixture was stirred over night at room temperature. After evaporation of the solvent the residue was dissolved in methanol and given on a PoraPak Rxn CX column. The column was washed with 100 mL methanol, and the product was eluted with methanol/ammonia. The solvent was removed, and the residue was purified by HPLC yielding 32.8 mg of the title compound.

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in methanol
  3. washThe column was washed with 100 mL methanol
  4. washthe product was eluted with methanol/ammonia
  5. customThe solvent was removed
  6. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-ac451422c6d545488c50f47bc64f19a8
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987286B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes