Trifluoroacetic acid → 1-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

HRID 592489Notes

Reaction equation

HRID 592489 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:11]1([C:14]2[CH:51]=[CH:50][CH:49]=[CH:48][C:15]=2[CH2:16][CH2:17][C:18]2[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][N:21]=[C:20]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([CH:35]4[CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37][CH2:36]4)=[N:33][CH:34]=3)[N:19]=2)[CH2:13][CH2:12]1)(=[O:10])[NH2:9]>C(Cl)Cl>[NH:38]1[CH2:37][CH2:36][CH:35]([C:32]2[N:33]=[CH:34][C:29]([NH:28][C:20]3[N:19]=[C:18]([CH2:17][CH2:16][C:15]4[CH:48]=[CH:49][CH:50]=[CH:51][C:14]=4[C:11]4([C:8]([NH2:9])=[O:10])[CH2:12][CH2:13]4)[C:23]([C:24]([F:26])([F:25])[F:27])=[CH:22][N:21]=3)=[CH:30][CH:31]=2)[CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712293tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate

Product 1

HCID 732964281-(2-(2-(2-((6-(Piperidin-4-yl)pyridin-3-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.50 mL, 6.5 mmol) was added to a mixture of tert-Butyl 4-(5-((4-(2-(1-carbamoylcyclopropyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate A79 (0.080 g, 0.13 mmol) in DCM (5 mL) and the mixture stirred for 4 hours. The mixture was concentrated under reduced pressure and quenched with 25% aqueous NaOH (20 mL) before extracting with EtOAc (3×20 mL). The combined organic extracts were concentrated under reduced pressure and the above procedure repeated with DCM (1.5 mL) and TFA (0.2 mL) for 3 hours. The mixture was concentrated under reduced pressure and quenched with 25% aqueous NaOH (20 mL) before extracting with EtOAc (3×20 mL). The combined organic residues were dried (phase separation cartridge) and concentrated under reduced pressure to give the title compound 68 (0.069 g, quantitative). LCMS-A: rt 4.783 min; m/z 511.3 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customquenched with 25% aqueous NaOH (20 mL)
  3. extractionbefore extracting with EtOAc (3×20 mL)
  4. concentrationThe combined organic extracts were concentrated under reduced pressure
  5. waitthe above procedure repeated with DCM (1.5 mL) and TFA (0.2 mL) for 3 hours
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customquenched with 25% aqueous NaOH (20 mL)
  8. extractionbefore extracting with EtOAc (3×20 mL)
  9. customThe combined organic residues were dried
  10. custom(phase separation cartridge)
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-214c813319ce40f79b45db27f452daa2
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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