Trifluoroacetic acid → 5-(6-(4-aminopiperidin-1-yl)pyridin-3-yl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-N-((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamide

HRID 1530351Notes

Reaction equation

HRID 1530351 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([C:26](=[O:40])[NH:27][CH2:28][C:29]4[C:30](=[O:39])[NH:31][C:32]([CH3:38])=[CH:33][C:34]=4[CH:35]([CH3:37])[CH3:36])[C:23]([CH3:41])=[C:22]([N:42]([CH2:49][CH3:50])[CH:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:15]=[CH:16][C:17]([C:20]3[CH:21]=[C:22]([N:42]([CH2:49][CH3:50])[CH:43]4[CH2:44][CH2:45][O:46][CH2:47][CH2:48]4)[C:23]([CH3:41])=[C:24]([CH:25]=3)[C:26]([NH:27][CH2:28][C:29]3[C:30](=[O:39])[NH:31][C:32]([CH3:38])=[CH:33][C:34]=3[CH:35]([CH3:37])[CH3:36])=[O:40])=[CH:18][CH:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86672674tert-butyl (1-(5-(3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-(((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-4-methylphenyl)pyridin-2-yl)piperidin-4-yl)carbamate

Product 1

HCID 708727265-(6-(4-aminopiperidin-1-yl)pyridin-3-yl)-3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-N-((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methylbenzamideYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-butyl(1-(5-(3-(ethyl(tetrahydro-2H-pyran-4-yl)amino)-5-(((4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-4-methylphenyl)pyridin-2-yl)piperidin-4-yl)carbamate (0.31 g, 0.44 mmol) was taken in DCM (5 mL) and TFA (1 mL) was added to it and stirred at rt for 2 h. After completion of reaction, solvent was removed under reduced pressure and saturated NaHCO3 solution was added to it. Extraction was carried out using 10% MeOH/DCM; the combined organic layers were washed with water and brine; dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure to give the title compound (0.26 g, 98.11%)

Workup

  1. customAfter completion of reaction, solvent
  2. customwas removed under reduced pressure and saturated NaHCO3 solution
  3. additionwas added to it
  4. extractionExtraction
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3bd961bba1441efb25afde90559ca41
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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