HCID 178523501, compound → HCID 178507516, compound

HRID 1093609Notes

Reaction equation

HRID 1093609 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13](=[O:29])[CH2:14][NH:15][C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[NH:20][N:19]=2)=[O:17])[CH2:9][CH2:8]1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[O:6][CH:7]1[CH2:8][CH2:9][N:10]([C:13](=[O:29])[CH2:14][NH:15][C:16]([C:18]2[CH:22]=[C:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:20][N:19]=2)=[O:17])[CH2:11][CH2:12]1

Participants

5

Reactant 1

HCID 178523501HCID 178523501, compound

Product 1

HCID 178507516HCID 178507516, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-nitro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide (0.07 g, 0.00016 mole) in a mixture of methanol (5 mL) and THF (5 mL) was added 10% Pd/C (0.01 g). The resulting mixture was stirred under an atmosphere of hydrogen for 30 minutes. The mixture was then filtered through celite, and the celite was washed with methanol. The combined organic layers were concentrated under reduced pressure. The resulting residue was re-crystallized from a hexane/chloroform mixture to afford 0.025 g (39%) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-amino-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 420.2 (M+1)+, 96.9%, 1H NMR (DMSO-d6): δ 8.1 (bs, 1H), 7.8 (d, 2H), 7.5-7.3 (m, 3H), 7.1 (m, 1H), 6.85 (d, 1H), 6.7 (m, 2H), 6.5 (m, 1H), 4.7 (s, 2H), 4.6 (s, 1H), 4.2 (s, 2H), 3.9 (m, 2H), 2.0 (m, 2H), 1.8 (m, 2H), 1.4 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe celite was washed with methanol
  3. concentrationThe combined organic layers were concentrated under reduced pressure
  4. customThe resulting residue was re-crystallized from a hexane/chloroform mixture

Sources & evidence

ORD record
ord-f3385135ca8a4f6d82eec0ae69c7e23f
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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