4-[5-(4-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester → N-(4-tert-Butyl-phenyl)-6-piperazin-1-yl-nicotinamide

HRID 2190542Notes

Reaction equation

HRID 2190542 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:32])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([NH:21][C:20](=[O:32])[C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][CH:16]=2)=[CH:27][CH:26]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 593180214-[5-(4-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59318019N-(4-tert-Butyl-phenyl)-6-piperazin-1-yl-nicotinamideYield 58.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-[5-(4-tert-Butyl-phenylcarbamoyl)-pyridin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester (200 mg, 0.45 mmol) was dissolved at rt in a mixture of 30% TFA in CH2Cl2. The reaction mixture was stirred until TLC indicated consumption of starting material (30 min). The mixture was then partitioned between EtOAc and water. The water layer was basified with solid NaOH to pH 12. The organic layer was separated and the aqueous layer was extracted again with EtOAc. The combined organic layer was washed with water, dried over Na2SO4, filtered and concentrated to afford the product (89 mg, Yield: 56%). HRMS m/z calcd for C20H26N4O [M+H]+: 339.2180. Found: 339.2180.

Workup

  1. customconsumption of starting material (30 min)
  2. customThe mixture was then partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted again with EtOAc
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9f2540f70ebb4677a193e44689c31c1f
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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