HCID 178436409, compound → HCID 178436408, compound

HRID 1396995Notes

Reaction equation

HRID 1396995 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:27][C:28](=[O:38])[NH:29][O:30]CC2C=CC=CC=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[N+:19]=3[O-:26])=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:27][C:28]([NH:29][OH:30])=[O:38])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH3:25])[N+:19]=3[O-:26])=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 178436409HCID 178436409, compound

Product 1

HCID 178436408HCID 178436408, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(5S)-1-((2R)-2-(Cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(6-ethyl-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (61 mg, 0.12 mmol) was dissolved in methanol (8 mL), and Pearlman's catalyst (16 mg, 0.02 mmol) was added. The resulting mixture was stirred under 1 atm of H2 for 30 min. After 30 min, the mixture was filtered, concentrated, and purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O) to afford (5S)-1-[(2R)-2-(cyclopentylmethyl)-4-(hydroxyamino)-4-oxobutanoyl]-N-(6-ethyl-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (35 mg, 0.08 mmol, 68% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.01-1.23 (m, 2H) 1.34 (s, 3H) 1.43-1.65 (m, 5H) 1.70-1.77 (m, 1H) 1.79-1.92 (m, 3H) 2.21-2.37 (m, 1H) 2.42-2.57 (m, 1H) 2.87-3.04 (m, 2H) 3.81-3.96 (m, 1H) 5.11-5.20 (m, 1H) 7.10-7.24 (m, 2H) 7.45-7.56 (m, 1H) 8.30-8.40 (m, 1H). MS: 432 ([M+H]+).

Workup

  1. waitAfter 30 min
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated
  4. custompurified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O)

Sources & evidence

ORD record
ord-ed5d7db3983c4c7b9c423ae57fe39c7f
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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