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Trifluoroacetic acid → 2-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

HRID 592477
Notes
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Reaction equation

HRID 592477 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:50])[CH:10]([C:12]1[CH:49]=[CH:48][CH:47]=[CH:46][C:13]=1[CH2:14][CH2:15][C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[C:18]([NH:26][C:27]2[CH:28]=[CH:29][C:30]([CH:33]3[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]3)=[N:31][CH:32]=2)[N:17]=1)[CH3:11]>C(Cl)Cl>[NH:36]1[CH2:37][CH2:38][CH:33]([C:30]2[N:31]=[CH:32][C:27]([NH:26][C:18]3[N:17]=[C:16]([CH2:15][CH2:14][C:13]4[CH:46]=[CH:47][CH:48]=[CH:49][C:12]=4[CH:10]([CH3:11])[C:9]([NH2:8])=[O:50])[C:21]([C:22]([F:24])([F:23])[F:25])=[CH:20][N:19]=3)=[CH:28][CH:29]=2)[CH2:34][CH2:35]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712343tert-Butyl 4-(5-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 732952962-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamideYield 134%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

TFA (0.50 mL, 6.5 mmol) was added to tert-butyl 4-(5-((4-(2-(1-amino-1-oxopropan-2-yl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A72 (0.060 g, 0.099 mmol) in DCM (5 mL) and the mixture was stirred for 2 hours. The mixture was concentrated under reduced pressure and quenched with 25% aq. NaOH (20 mL). The aqueous phase was extracted with EtOAc (3×20 mL) before the combined organics were dried (phase separation cartridge) and concentrated under reduced pressure. The suspension was sonicated with hexane and concentrated under reduced pressure to give the title compound (0.066 g, 134% residual solvent/water). LCMS-D: rt 3.025 min; m/z 499.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customquenched with 25% aq. NaOH (20 mL)
  3. extractionThe aqueous phase was extracted with EtOAc (3×20 mL) before the combined
  4. customorganics were dried
  5. custom(phase separation cartridge)
  6. concentrationconcentrated under reduced pressure
  7. customThe suspension was sonicated with hexane
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-975140aeb688436383aae2a33f486009
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09238644B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes