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Hydrochloric Acid → 5-(Piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine

HRID 2047114
Notes
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Reaction equation

HRID 2047114 reaction equation
C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)[CH:9]=1.C(O)C.O.Cl>O1CCOCC1.C(Cl)Cl>[NH:30]1[CH2:31][CH2:32][CH:27]([C:10]2[CH:9]=[C:8]([NH2:7])[N:13]3[N:14]=[CH:15][C:16]([C:17]4[CH:18]=[N:19][C:20]5[C:25]([CH:26]=4)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[C:12]3[N:11]=2)[CH2:28][CH2:29]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 67494438tert-Butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate

Product 1

HCID 667380825-(Piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amineYield 73.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a 20 mL scintillation vial was charged tert-butyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)-amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidine-1-carboxylate (80 μmol, 56 mg) followed by ethanol (2 mL) and H2O (500 μL). To this solution was added 2 mL of 4N HCl in 1,4-dioxane. This solution was heated to 60° C. for 2 hours. Upon completion, the reaction mixture was diluted with DCM (10 mL) and washed with NaHCO3(aq) and extracted with DCM twice more. The combined organics were then dried over Na2SO4 and the solvent was removed in vacuo to yield 5-(piperidin-4-yl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine (20.3 mg, 59 umol) as cream-colored solid

Workup

  1. washwashed with NaHCO3(aq)
  2. extractionextracted with DCM twice more
  3. dry with materialThe combined organics were then dried over Na2SO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-795558556ec54a31a4acb3bdba84d75e
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08591943B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes