N-(3-fluoro-4-piperazin-1-yl-phenyl)-2-pyridin-3-yl-benzamide → Ammonia

HRID 2196187Notes

Reaction equation

HRID 2196187 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15](=[O:28])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH2:29]([N:31]([CH2:46][CH3:47])[C:32]([CH:34](OS(C)(=O)=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33])[CH3:30]>CN(C=O)C>[NH3:8].[CH2:46]([N:31]([CH2:29][CH3:30])[C:32]([CH:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[N:11]1[CH2:12][CH2:13][N:8]([C:7]2[CH:6]=[CH:5][C:4]([NH:14][C:15](=[O:28])[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:3][C:2]=2[F:1])[CH2:9][CH2:10]1)=[O:33])[CH3:47]

Participants

5

Reactant 2

HCID 66931680N-(3-fluoro-4-piperazin-1-yl-phenyl)-2-pyridin-3-yl-benzamideHCID 76688989Methanesulfonic acid diethylcarbamoyl-phenyl-methyl ester

Product 2

HCID 222AmmoniaHCID 25134625Jnj-31020028

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-fluoro-4-piperazin-1-yl-phenyl)-2-pyridin-3-yl-benzamide (0.16 g, 0.4 mmol) and methanesulfonic acid diethylcarbamoyl-phenyl-methyl ester (0.06 g, 0.2 mmol) in DMF (1 mL) was heated at 50° C. After five hours, the reaction mixture was quenched with H2O (5 mL) and extracted with EtOAc (4×10 mL). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure. Chromatography of the residue (SiO2: NH3 (MeOH):CH2Cl2) yielded the title compound.

Workup

  1. customthe reaction mixture was quenched with H2O (5 mL)
  2. extractionextracted with EtOAc (4×10 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e999bf2ba2384cc9be087ce57f12118d
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

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