HCID 178523481, compound → 5-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093650Notes

Reaction equation

HRID 1093650 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[O:31]CC3C=CC=CC=3)[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:39])[CH2:16][NH:17][C:18]([C:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[NH:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 178523481HCID 178523481, compound

Product 1

HCID 1785234825-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amideYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 5-(2-benzyloxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.2 g, 0.00039 mole) in methanol (60 mL), added 10% Pd/C (0.04 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 2 hours. The mixture was then filtered through celite, the celite was washed with methanol and the organic layers were concentrated under reduced pressure. The residue was recrystallized from a mixture of ethyl acetate and methanol to afford 0.055 g (32%) of 5-(2-hydroxy-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 454.16 (M+1)+, 94.65%. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 10.4 (s, 1H), 8.0 (s, 1H), 7.6 (d, 1H), 7.2 (m, 4H), 7.0 (d, 1H), 6.8 (m, 2H), 6.6 (t, 1H), 4.9 (d, 1H), 4.3 (d, 1H), 4.2 (d, 2H), 3.8 (d, 1H), 3.6 (m, 1H), 3.2 (t, 1H), 2.7 (t, 1H), 1.9 (m, 2H), 1.3 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe celite was washed with methanol
  3. concentrationthe organic layers were concentrated under reduced pressure
  4. customThe residue was recrystallized from a mixture of ethyl acetate and methanol

Sources & evidence

ORD record
ord-0f1c226635414e1ba0c30f2a98c8812e
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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