HCID 57874511, compound → 5-(2-Hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093648Notes

Reaction equation

HRID 1093648 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)[O:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1>CO.C1COCC1.[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])[O:22][N:21]=2)=[O:19])[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 57874511HCID 57874511, compound

Product 1

HCID 1359151885-(2-Hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amideYield 16.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(2-benzyloxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.142 g, 0.00026 mole) in a mixture of methanol (60 mL) and THF (10 mL) was added 10% Pd/C (0.05 g) and the resulting mixture was stirred under an atmosphere of hydrogen for 1 hour. The mixture was then filtered through celite, the celite was washed with methanol and the organic layers were concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to afford 0.02 g (13%) of 5-(2-hydroxy-phenyl)-isoxazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 455.14 (M+1)+. 94.82%, 1H NMR (DMSO-d6): δ 10.8 (s, 1H), 8.7 (t, 1H), 7.81 (d, 1H), 7.38 (t, 1H), 7.25 (d, 1H), 7.0 (m, 4H), 6.8 (d, 1H), 6.6 (t, 1H), 4.9 (d, 1H), 4.3 (d, 1H), 4.1 (d, 2H), 3.9 (d, 1H), 3.6 (s, 1H), 3.2 (m, 1H), 2.7 (m, 1H), 2.2 (m, 2H), 1.5 (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 resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-66e835529eac4c1f89ec0db9e0d87d64
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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