HCID 178523397, compound → HCID 178523981, compound

HRID 1396947Notes

Reaction equation

HRID 1396947 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:25][N:26]([CH:35]=[O:36])[O:27]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]=[CH:20][N+:19]=3[O-:24])=[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]([CH2:25][N:26]([CH:35]=[O:36])[OH:27])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N+:19]=3[O-:24])=[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 178523397HCID 178523397, compound

Product 1

HCID 178523981HCID 178523981, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

In a 50 mL round-bottomed flask was added (5S)-1-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-N-(1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (67 mg, 0.136 mmol) in methanol (3 ml), followed by Pearlman's catalyst (7 mg). The mixture was stirred under a balloon of H2 for 35 min, then catalyst was filtered off. Removal of the solvent provided (5S)-1-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide as a colorless oil. (27 mg, 48%). LCMS: (M+H)+: 404.3. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.04-1.26 (m, 2H) 1.40-1.70 (m, 5H) 1.70-2.00 (m, 4H) 3.35-3.45 (m, 1H) 3.50-3.75 (m, 2H) 3.76-4.04 (m, 2H) 5.10-5.37 (m, 1H) 7.09-7.34 (m, 2H) 7.49-7.67 (m, 1H) 7.91 (s, 1H) 8.35 (d, J=6.57 Hz, 1H) 8.46 (dd, J=8.46, 1.64 Hz, 1H)

Workup

  1. filtrationcatalyst was filtered off
  2. customRemoval of the solvent

Sources & evidence

ORD record
ord-dfb4c5283ffa4de19a910ac91e1e2072
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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